Those of you who use Mail with Gmail, how the hell do you do it?

Discussion in 'OS X El Capitan (10.11)' started by baryon, Jul 12, 2016.

  1. baryon, Jul 12, 2016
    Last edited: Jul 12, 2016

    baryon macrumors 68040

    baryon

    Joined:
    Oct 3, 2009
    #1
    TLDR: OS X El Capitan 10.11.5, Mail.app, Gmail, 2013 Retina MacBook Pro. Mail randomly refuses to send and/or receive mail. I've tried everything I could find online about this exact issue, nothing has helped so far. I think it was fine in Yosemite, it was definitely fine in Mavericks and before.

    So someone calls me and says "hey did you get my email?". I say "no, let me refresh it just in case", and press the "Get Mail" button in Gmail. It says "Checking for mail...". It says that for far too many seconds, and nothing happens. So I go to Gmail.com, which I rarely do, and I find a new message, sent 2 hours ago. 10 minutes later, Mail still says "Checking for Mail...".

    This happens all the damn time. Sometimes it works, but when I have important stuff to do, it doesn't work. I sometimes send a message and it says "Sending..." for about 10 minutes, then I cancel it and send it again. Then both messages get sent eventually even though both are sitting in Outbox. So I think it's still not sent, and delete the message and resend it from gmail.com. Then it gets sent 3 times in total, which I only find out much later, when mail finally removes it from Outbox.

    Then I get exclamation marks next to my Inbox in Mail. When I click on it it says something about outgoing mail servers, which I have checked and is correctly set up (as proved by the fact that messages do eventually get sent).

    I have deleted all the mail cache, I have turned off my gmail account in OS X, I have deleted everything from Mail and started from scratch. I have done this 3 times so far, no luck. I'm out of ideas.

    How do I send and receive emails with Mail? I may have 10 years of experience with complicated software but I'm probably too ****ing dumb to figure out how to send a ****ing email with the "world's most advanced operating system" (don't make me laugh).

    I'd post screenshots but I just deleted my entire mail account so there's nothing there. Could someone please just tell me how it's supposed to be set up with Gmail for it to actually work without any issues?

    Also, could you recommend any free apps that are as much like Mail as possible, except they actually work?
     
  2. hallux macrumors 68020

    hallux

    Joined:
    Apr 25, 2012
    #2
    Mine just works (is that trademarked by Apple?). I've had it set up since Mavericks at least. I have 2-factor authentication set up on my Google account but I've configured my Google account on my Mac using an app-specific password.
     
  3. simon lefisch macrumors 6502a

    simon lefisch

    Joined:
    Sep 29, 2014
    #3
    When I did a clean install of El Cap when it was first released, I setup my gmail like normal. Been working working fine ever since.

    Is 2-factor enabled in your gmail (website)? If so, that could be the prob.
     
  4. NoBoMac macrumors 6502a

    Joined:
    Jul 1, 2014
    #4
    Using a VPN? Seen oddness in the past when VPNs are in use.

    Oh, and: my Gmail works with stock Mail.app. Using app-specific password, can't recall if I had to create new ones for El Capitan.
     
  5. Sital macrumors 68000

    Sital

    Joined:
    May 31, 2012
    Location:
    New England
    #5
    I hear ya, OP. With El Capitan (I forget which .x version it started with) I started getting exclamation points on my accounts multiple times a day. That has been the only problem I've had with El Capitan and, prior to that, I had been using Mail for years with no issues. I ended up switching to Airmail (first the beta version to try it out, then the paid App Store version) and have had no problems with my Gmail accounts since.
     
  6. BrianBaughn macrumors 601

    BrianBaughn

    Joined:
    Feb 13, 2011
    Location:
    Baltimore, Maryland
    #6
    I suggest setting up and logging into a new, temporary User Account on your Mac, adding the Gmail account and checking its usability.

    This will probably end up showing that it's an issue that exists in your own User Account...important to pinpoint this.
     
  7. MacGizmo macrumors 6502a

    MacGizmo

    Joined:
    Apr 27, 2003
    Location:
    Arizona
    #7
    You get what you pay for. There are no free apps like Mail. There are plenty of excellent and fairly cheap apps that will handle Gmail. Airmail is my favorite.
     
  8. baryon thread starter macrumors 68040

    baryon

    Joined:
    Oct 3, 2009
    #8
    Thanks everyone! I will try making a new user account to see if it happens there too, and in the meantime I'm using good old gmail online. With the preview pane extension it's actually not that lame. It's good to know that not everyone has the problem, so it can probably be fixed somehow.
     
  9. steve23094 macrumors 68000

    steve23094

    Joined:
    Apr 23, 2013
    #9
    I migrated away from Gmail to iCloud a few years ago. Gmail often has problems with Apple software and I got sick of it. It's because Gmail handles mail in their own way, not using the standards everybody else does. Having mail tags instead of folders for example is a smarter way to do things but it's a recipe for incompatibility problems as you have discovered.
     
  10. lah macrumors regular

    Joined:
    Mar 22, 2010
    #10
    me too - I'm pretty frustrated with Mail.app and Gmail (i use it with my work account).
    Mail.app will work fine for some stretches then it just stops working. I will have to reboot the computer to get it back up and running. Or sometimes I don't get all my emails, i only find out about the missing emails when I check my phone.
    I've tried using Outlook - works well with gmail - but not a good experience.
    I've started using postbox this past week. The gmail connection is rock solid but I find the app not as polished as mail.app. Very rough around the edges and slow in my opinion, but I can get work done at the end of the day so I might stick with it.
     
  11. komatsu macrumors 6502

    Joined:
    Sep 19, 2010
    #11
    Thanks to OP for kindly highlighting this more than common issue.

    Mail+Gmail are not happy bedfellows unless you like yellow exclamation marks.
     
  12. MC6800 macrumors 6502

    Joined:
    Jun 29, 2016
    #12
    Have you tried Mail's Connection Doctor? That, the logs, and the Activity window should be giving you some good hints as to what's going on.
     
  13. grahamperrin macrumors 601

    grahamperrin

    Joined:
    Jun 8, 2007
    #13
    OK, that alone smells of a database inconsistency. Not a problem with Google's service; a local inconsistency.

    Widespread across the web, there are umpteen recommendations that, essentially, focus on an index file. So widespread that El Capitan questions such as this go unanswered:
    – smells of an inconsistency :)

    I'll make todays pick, from those umpteen: SpamSieve Manual: How can I rebuild Apple Mail’s database? – and I pick that, because it contains a first step that's missing from some other recommendations: Quit Mail.
     
  14. baryon thread starter macrumors 68040

    baryon

    Joined:
    Oct 3, 2009
    #14
    Thanks! I did try to delete everything from the "V3" folder before (so that includes what that article describes) and it didn't seem to fix the issue unfortunately... But I will try again on a day when I have more patience, who knows maybe I messed something up.
     
  15. grahamperrin macrumors 601

    grahamperrin

    Joined:
    Jun 8, 2007
    #15
    OK. When you run Disk Utility on the startup volume, is it apparently OK?
     
  16. baryon thread starter macrumors 68040

    baryon

    Joined:
    Oct 3, 2009
    #16
    Yes, Disk Utility's first aid reports that everything seems okay (green checkmark and all).
     
  17. baryon, Jul 30, 2016
    Last edited: Jul 30, 2016

    baryon thread starter macrumors 68040

    baryon

    Joined:
    Oct 3, 2009
    #17
    When I click on the exclamation mark in the triangle next to "Inbox", I get this message: Screen Shot 2016-07-30 at 11.26.20.png


    Connection Doctor looks like this:

    Screen Shot 2016-07-30 at 11.28.12.png

    The one that's spinning and says "Connecting to server..." just spins there forever.

    The Activity window is completely blank and empty.

    The logs are full of this:

    Code:
    Jul 30 11:33:17  Mail[1491] <Debug>: ERROR: Connecting failed for socket: 0x7fdad594d140, error: Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out"
    For the brief period when I also used my iCloud email address in Mail, the same issue would happen to iCloud, so it may not even be related to Gmail.

    While the exclamation mark is there next to Inbox, I can't receive mail. Sometimes I can't send mail, sometimes both. It usually resolves itself within a few hours if I do nothing, but Mail does spend about 50% of its time not working at all. Turning WiFi off and back on again always instantly fixes the issue, that could be a clue...

    Any ideas? Thank you so much for helping.
     
  18. imrazor macrumors member

    Joined:
    Sep 8, 2010
    #18
    Odd, that. I had lots of exclamation marks with Mail+Gmail in older versions of OS X, but El Cap seems to be handling it just fine. I *did* create a new user account for El Cap, because iCloud started flipping out a couple months after I upgraded.
     
  19. MC6800 macrumors 6502

    Joined:
    Jun 29, 2016
    #19
    My guess is that turning WIFI off/on is forcing it to restart the IMAP conversation. You should be able to see just where it's getting hung when it fails again by selecting that Google IMAP line in the Connection Doctor and then clicking Show Detail and Check Again.
     
  20. simon lefisch macrumors 6502a

    simon lefisch

    Joined:
    Sep 29, 2014
    #20
    @baryon, I would suggest you create another account and setup Mail with just Gmail and see if you have trouble connecting. If it connects without probs, it could be something with your user profile.
     
  21. baryon thread starter macrumors 68040

    baryon

    Joined:
    Oct 3, 2009
    #21
    Thanks! Here are the details from Connection Doctor when I select the IMAP connection:

    Code:
    INITIATING CONNECTION Jul 31 13:21:52.044 host:imap.gmail.com -- port:993 -- socket:0x0 -- thread:0x7fe089263d90
    
    INITIATING CONNECTION Jul 31 13:21:52.044 host:smtp.gmail.com -- port:587 -- socket:0x0 -- thread:0x7fe085f0a500
    
    CONNECTED Jul 31 13:21:52.086 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    
    READ Jul 31 13:21:52.125 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    220 smtp.gmail.com ESMTP c16sm11752358wme.4 - gsmtp
    
    CONNECTED Jul 31 13:21:52.129 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    
    WROTE Jul 31 13:21:52.137 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    EHLO [192.168.1.66]
    
    READ Jul 31 13:21:52.178 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    250-smtp.gmail.com at your service, [78.92.199.183]
    250-SIZE 35882577
    250-8BITMIME
    250-STARTTLS
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Jul 31 13:21:52.178 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    STARTTLS
    
    READ Jul 31 13:21:52.216 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    220 2.0.0 Ready to start TLS
    
    READ Jul 31 13:21:52.253 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    * OK Gimap ready for requests from 78.92.199.183 204mb249297099wmu
    
    WROTE Jul 31 13:21:52.254 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    1.119 CAPABILITY
    
    WROTE Jul 31 13:21:52.265 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    EHLO [192.168.1.66]
    
    READ Jul 31 13:21:52.296 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH2 AUTH=PLAIN AUTH=PLAIN-CLIENTTOKEN AUTH=OAUTHBEARER AUTH=XOAUTH
    1.119 OK Thats all she wrote! 204mb249297099wmu
    
    WROTE Jul 31 13:21:52.297 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    2.119 ID ("name" "Mac OS X Mail" "version" "9.3 (3124)" "os" "Mac OS X" "os-version" "10.11.6 (15G31)" "vendor" "Apple Inc.")
    
    READ Jul 31 13:21:52.337 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    * ID ("name" "GImap" "vendor" "Google, Inc." "support-url" "http://support.google.com/mail" "remote-host" "78.92.199.183" "connection-token" "204mb249297099wmu")
    2.119 OK Success 204mb249297099wmu
    
    WROTE Jul 31 13:21:52.337 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    3.119 AUTHENTICATE XOAUTH2 dXNlcj1tYXRlZG9icmF5QGdtYWlsLmNvbQFhdXRoPUJlYXJlciB5YTI5LkNqUXdBLThLcnRCTmRuc2tSdDQyeV9hdEtESFpkYnFCcmdMLUp1aFdROXhTbjI3X3NUY2xyMktFdEE2RFczZ1ZPVVJ0em5BeQEB
    
    READ Jul 31 13:21:52.381 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    250-smtp.gmail.com at your service, [78.92.199.183]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Jul 31 13:21:52.382 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    AUTH XOAUTH2 dXNlcj1tYXRlZG9icmF5QGdtYWlsLmNvbQFhdXRoPUJlYXJlciB5YTI5LkNqUXdBLThLcnRCTmRuc2tSdDQyeV9hdEtESFpkYnFCcmdMLUp1aFdROXhTbjI3X3NUY2xyMktFdEE2RFczZ1ZPVVJ0em5BeQEB
    
    READ Jul 31 13:21:52.399 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    + eyJzdGF0dXMiOiI0MDAiLCJzY2hlbWVzIjoiQmVhcmVyIiwic2NvcGUiOiJodHRwczovL21haWwuZ29vZ2xlLmNvbS8ifQ==
    
    WROTE Jul 31 13:21:52.399 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    AQ==
    
    READ Jul 31 13:21:52.434 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    334 eyJzdGF0dXMiOiI0MDAiLCJzY2hlbWVzIjoiQmVhcmVyIiwic2NvcGUiOiJodHRwczovL21haWwuZ29vZ2xlLmNvbS8ifQ==
    
    WROTE Jul 31 13:21:52.435 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    AQ==
    
    READ Jul 31 13:21:52.437 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    3.119 NO [AUTHENTICATIONFAILED] Invalid credentials (Failure)
    
    WROTE Jul 31 13:21:52.439 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    7.119 AUTHENTICATE PLAIN  (*** 88 bytes hidden ***)
    
    READ Jul 31 13:21:52.473 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    535-5.7.8 Username and Password not accepted. Learn more at
    535 5.7.8  https://support.google.com/mail/answer/14257 c16sm11752358wme.4 - gsmtp
    
    WROTE Jul 31 13:21:52.474 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    AUTH PLAIN  (*** 88 bytes hidden ***)
    
    READ Jul 31 13:21:52.657 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    7.119 NO [ALERT] Application-specific password required: https://support.google.com/accounts/answer/185833 (Failure)
    
    WROTE Jul 31 13:21:52.657 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    8.119 AUTHENTICATE PLAIN  (*** 64 bytes hidden ***)
    
    READ Jul 31 13:21:52.697 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 c16sm11752358wme.4 - gsmtp
    
    WROTE Jul 31 13:21:52.697 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    AUTH PLAIN  (*** 64 bytes hidden ***)
    
    READ Jul 31 13:21:53.092 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 c16sm11752358wme.4 - gsmtp
    
    WROTE Jul 31 13:21:53.093 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    AUTH LOGIN
    
    READ Jul 31 13:21:53.093 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    8.119 NO [ALERT] Application-specific password required: https://support.google.com/accounts/answer/185833 (Failure)
    
    WROTE Jul 31 13:21:53.094 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    10.119 LOGIN redacted@gmail.com **************************
    
    READ Jul 31 13:21:53.132 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    334 VXNlcm5hbWU6
    
    WROTE Jul 31 13:21:53.132 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    bWF0ZWRvYnJheUBnbWFpbC5jb20=
    
    READ Jul 31 13:21:53.170 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    334 UGFzc3dvcmQ6
    
    WROTE Jul 31 13:21:53.170 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    ********************************
    
    READ Jul 31 13:21:53.350 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    10.119 NO [ALERT] Application-specific password required: https://support.google.com/accounts/answer/185833 (Failure)
    
    WROTE Jul 31 13:21:53.351 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe0886600d0 -- thread:0x7fe089263d90
    11.119 LOGOUT
    
    READ Jul 31 13:21:53.377 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 c16sm11752358wme.4 - gsmtp
    
    WROTE Jul 31 13:21:53.378 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    AUTH LOGIN
    
    READ Jul 31 13:21:53.416 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    334 VXNlcm5hbWU6
    
    WROTE Jul 31 13:21:53.417 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    bWF0ZWRvYnJheUBnbWFpbC5jb20=
    
    READ Jul 31 13:21:53.455 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    334 UGFzc3dvcmQ6
    
    WROTE Jul 31 13:21:53.455 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    ********************************
    
    READ Jul 31 13:21:53.693 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 c16sm11752358wme.4 - gsmtp
    
    WROTE Jul 31 13:21:53.693 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0887733a0 -- thread:0x7fe085f0a500
    QUIT
    

    ... and here's when I select the SMTP connection (which also failed now):

    Code:
    CONNECTED Jul 31 13:23:39.295 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    
    READ Jul 31 13:23:39.336 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    220 smtp.gmail.com ESMTP va3sm25253415wjb.18 - gsmtp
    
    WROTE Jul 31 13:23:39.346 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    EHLO [192.168.1.66]
    
    READ Jul 31 13:23:39.389 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    250-smtp.gmail.com at your service, [78.92.199.183]
    250-SIZE 35882577
    250-8BITMIME
    250-STARTTLS
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Jul 31 13:23:39.390 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    STARTTLS
    
    READ Jul 31 13:23:39.429 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    220 2.0.0 Ready to start TLS
    
    CONNECTED Jul 31 13:23:39.463 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    
    READ Jul 31 13:23:39.463 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    * OK Gimap ready for requests from 78.92.199.183 dg5mb77219305wjd
    
    WROTE Jul 31 13:23:39.464 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    1.123 CAPABILITY
    
    WROTE Jul 31 13:23:39.471 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    EHLO [192.168.1.66]
    
    READ Jul 31 13:23:39.503 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH2 AUTH=PLAIN AUTH=PLAIN-CLIENTTOKEN AUTH=OAUTHBEARER AUTH=XOAUTH
    1.123 OK Thats all she wrote! dg5mb77219305wjd
    
    WROTE Jul 31 13:23:39.503 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    2.123 ID ("name" "Mac OS X Mail" "version" "9.3 (3124)" "os" "Mac OS X" "os-version" "10.11.6 (15G31)" "vendor" "Apple Inc.")
    
    READ Jul 31 13:23:39.543 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    * ID ("name" "GImap" "vendor" "Google, Inc." "support-url" "http://support.google.com/mail" "remote-host" "78.92.199.183" "connection-token" "dg5mb77219305wjd")
    2.123 OK Success dg5mb77219305wjd
    
    WROTE Jul 31 13:23:39.544 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    3.123 AUTHENTICATE XOAUTH2 dXNlcj1tYXRlZG9icmF5QGdtYWlsLmNvbQFhdXRoPUJlYXJlciB5YTI5LkNqUXdBLThLcnRCTmRuc2tSdDQyeV9hdEtESFpkYnFCcmdMLUp1aFdROXhTbjI3X3NUY2xyMktFdEE2RFczZ1ZPVVJ0em5BeQEB
    
    READ Jul 31 13:23:39.589 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    250-smtp.gmail.com at your service, [78.92.199.183]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Jul 31 13:23:39.590 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    AUTH XOAUTH2 dXNlcj1tYXRlZG9icmF5QGdtYWlsLmNvbQFhdXRoPUJlYXJlciB5YTI5LkNqUXdBLThLcnRCTmRuc2tSdDQyeV9hdEtESFpkYnFCcmdMLUp1aFdROXhTbjI3X3NUY2xyMktFdEE2RFczZ1ZPVVJ0em5BeQEB
    
    READ Jul 31 13:23:39.645 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    334 eyJzdGF0dXMiOiI0MDAiLCJzY2hlbWVzIjoiQmVhcmVyIiwic2NvcGUiOiJodHRwczovL21haWwuZ29vZ2xlLmNvbS8ifQ==
    
    WROTE Jul 31 13:23:39.645 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    AQ==
    
    READ Jul 31 13:23:39.665 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    + eyJzdGF0dXMiOiI0MDAiLCJzY2hlbWVzIjoiQmVhcmVyIiwic2NvcGUiOiJodHRwczovL21haWwuZ29vZ2xlLmNvbS8ifQ==
    
    WROTE Jul 31 13:23:39.666 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    AQ==
    
    READ Jul 31 13:23:39.684 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    535-5.7.8 Username and Password not accepted. Learn more at
    535 5.7.8  https://support.google.com/mail/answer/14257 va3sm25253415wjb.18 - gsmtp
    
    WROTE Jul 31 13:23:39.685 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    AUTH PLAIN  (*** 88 bytes hidden ***)
    
    READ Jul 31 13:23:39.705 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    3.123 NO [AUTHENTICATIONFAILED] Invalid credentials (Failure)
    
    WROTE Jul 31 13:23:39.706 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    7.123 AUTHENTICATE PLAIN  (*** 88 bytes hidden ***)
    
    READ Jul 31 13:23:39.916 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    7.123 NO [ALERT] Application-specific password required: https://support.google.com/accounts/answer/185833 (Failure)
    
    WROTE Jul 31 13:23:39.916 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    8.123 AUTHENTICATE PLAIN  (*** 64 bytes hidden ***)
    
    READ Jul 31 13:23:39.944 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 va3sm25253415wjb.18 - gsmtp
    
    WROTE Jul 31 13:23:39.945 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    AUTH PLAIN  (*** 64 bytes hidden ***)
    
    READ Jul 31 13:23:40.133 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    8.123 NO [ALERT] Application-specific password required: https://support.google.com/accounts/answer/185833 (Failure)
    
    WROTE Jul 31 13:23:40.134 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    10.123 LOGIN redacted@gmail.com **************************
    
    READ Jul 31 13:23:40.160 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 va3sm25253415wjb.18 - gsmtp
    
    WROTE Jul 31 13:23:40.160 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    AUTH LOGIN
    
    READ Jul 31 13:23:40.203 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    334 VXNlcm5hbWU6
    
    WROTE Jul 31 13:23:40.204 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    bWF0ZWRvYnJheUBnbWFpbC5jb20=
    
    READ Jul 31 13:23:40.244 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    334 UGFzc3dvcmQ6
    
    WROTE Jul 31 13:23:40.244 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    ********************************
    
    READ Jul 31 13:23:40.418 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    10.123 NO [ALERT] Application-specific password required: https://support.google.com/accounts/answer/185833 (Failure)
    
    WROTE Jul 31 13:23:40.418 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe089124560 -- thread:0x7fe088511d40
    11.123 LOGOUT
    
    READ Jul 31 13:23:40.465 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 va3sm25253415wjb.18 - gsmtp
    
    WROTE Jul 31 13:23:40.466 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    AUTH LOGIN
    
    READ Jul 31 13:23:40.511 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    334 VXNlcm5hbWU6
    
    WROTE Jul 31 13:23:40.511 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    bWF0ZWRvYnJheUBnbWFpbC5jb20=
    
    READ Jul 31 13:23:40.550 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    334 UGFzc3dvcmQ6
    
    WROTE Jul 31 13:23:40.551 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    ********************************
    
    READ Jul 31 13:23:40.776 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 va3sm25253415wjb.18 - gsmtp
    
    WROTE Jul 31 13:23:40.777 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe085fb58c0 -- thread:0x7fe0891198a0
    QUIT
    
    INITIATING CONNECTION Jul 31 13:24:15.974 host:imap.gmail.com -- port:993 -- socket:0x0 -- thread:0x7fe088dcf3a0
    
    INITIATING CONNECTION Jul 31 13:24:15.974 host:smtp.gmail.com -- port:587 -- socket:0x0 -- thread:0x7fe085e7e5d0
    
    CONNECTED Jul 31 13:24:16.016 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    
    READ Jul 31 13:24:16.056 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    220 smtp.gmail.com ESMTP i7sm25209112wjg.42 - gsmtp
    
    WROTE Jul 31 13:24:16.065 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    EHLO [192.168.1.66]
    
    READ Jul 31 13:24:16.104 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    250-smtp.gmail.com at your service, [78.92.199.183]
    250-SIZE 35882577
    250-8BITMIME
    250-STARTTLS
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Jul 31 13:24:16.105 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    STARTTLS
    
    READ Jul 31 13:24:16.146 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    220 2.0.0 Ready to start TLS
    
    WROTE Jul 31 13:24:16.184 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    EHLO [192.168.1.66]
    
    CONNECTED Jul 31 13:24:16.209 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    
    READ Jul 31 13:24:16.209 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    * OK Gimap ready for requests from 78.92.199.183 uw3mb92067520wjc
    
    WROTE Jul 31 13:24:16.209 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    1.125 CAPABILITY
    
    READ Jul 31 13:24:16.249 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH2 AUTH=PLAIN AUTH=PLAIN-CLIENTTOKEN AUTH=OAUTHBEARER AUTH=XOAUTH
    1.125 OK Thats all she wrote! uw3mb92067520wjc
    
    WROTE Jul 31 13:24:16.249 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    2.125 ID ("name" "Mac OS X Mail" "version" "9.3 (3124)" "os" "Mac OS X" "os-version" "10.11.6 (15G31)" "vendor" "Apple Inc.")
    
    READ Jul 31 13:24:16.288 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    * ID ("name" "GImap" "vendor" "Google, Inc." "support-url" "http://support.google.com/mail" "remote-host" "78.92.199.183" "connection-token" "uw3mb92067520wjc")
    2.125 OK Success uw3mb92067520wjc
    
    WROTE Jul 31 13:24:16.289 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    3.125 AUTHENTICATE XOAUTH2 dXNlcj1tYXRlZG9icmF5QGdtYWlsLmNvbQFhdXRoPUJlYXJlciB5YTI5LkNqUXdBLThLcnRCTmRuc2tSdDQyeV9hdEtESFpkYnFCcmdMLUp1aFdROXhTbjI3X3NUY2xyMktFdEE2RFczZ1ZPVVJ0em5BeQEB
    
    READ Jul 31 13:24:16.300 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    250-smtp.gmail.com at your service, [78.92.199.183]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Jul 31 13:24:16.301 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    AUTH XOAUTH2 dXNlcj1tYXRlZG9icmF5QGdtYWlsLmNvbQFhdXRoPUJlYXJlciB5YTI5LkNqUXdBLThLcnRCTmRuc2tSdDQyeV9hdEtESFpkYnFCcmdMLUp1aFdROXhTbjI3X3NUY2xyMktFdEE2RFczZ1ZPVVJ0em5BeQEB
    
    READ Jul 31 13:24:16.351 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    + eyJzdGF0dXMiOiI0MDAiLCJzY2hlbWVzIjoiQmVhcmVyIiwic2NvcGUiOiJodHRwczovL21haWwuZ29vZ2xlLmNvbS8ifQ==
    
    WROTE Jul 31 13:24:16.351 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    AQ==
    
    READ Jul 31 13:24:16.357 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    334 eyJzdGF0dXMiOiI0MDAiLCJzY2hlbWVzIjoiQmVhcmVyIiwic2NvcGUiOiJodHRwczovL21haWwuZ29vZ2xlLmNvbS8ifQ==
    
    WROTE Jul 31 13:24:16.357 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    AQ==
    
    READ Jul 31 13:24:16.394 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    535-5.7.8 Username and Password not accepted. Learn more at
    535 5.7.8  https://support.google.com/mail/answer/14257 i7sm25209112wjg.42 - gsmtp
    
    READ Jul 31 13:24:16.395 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    3.125 NO [AUTHENTICATIONFAILED] Invalid credentials (Failure)
    
    WROTE Jul 31 13:24:16.395 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    AUTH PLAIN  (*** 88 bytes hidden ***)
    
    WROTE Jul 31 13:24:16.396 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    7.125 AUTHENTICATE PLAIN  (*** 88 bytes hidden ***)
    
    READ Jul 31 13:24:16.641 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 i7sm25209112wjg.42 - gsmtp
    
    WROTE Jul 31 13:24:16.641 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    AUTH PLAIN  (*** 64 bytes hidden ***)
    
    READ Jul 31 13:24:16.667 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    7.125 NO [ALERT] Application-specific password required: https://support.google.com/accounts/answer/185833 (Failure)
    
    WROTE Jul 31 13:24:16.668 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    8.125 AUTHENTICATE PLAIN  (*** 64 bytes hidden ***)
    
    READ Jul 31 13:24:16.874 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 i7sm25209112wjg.42 - gsmtp
    
    WROTE Jul 31 13:24:16.875 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    AUTH LOGIN
    
    READ Jul 31 13:24:16.913 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    334 VXNlcm5hbWU6
    
    WROTE Jul 31 13:24:16.913 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    bWF0ZWRvYnJheUBnbWFpbC5jb20=
    
    READ Jul 31 13:24:16.934 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    8.125 NO [ALERT] Application-specific password required: https://support.google.com/accounts/answer/185833 (Failure)
    
    WROTE Jul 31 13:24:16.934 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    10.125 LOGIN redacted@gmail.com **************************
    
    READ Jul 31 13:24:16.951 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    334 UGFzc3dvcmQ6
    
    WROTE Jul 31 13:24:16.951 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    ********************************
    
    READ Jul 31 13:24:17.146 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    10.125 NO [ALERT] Application-specific password required: https://support.google.com/accounts/answer/185833 (Failure)
    
    WROTE Jul 31 13:24:17.147 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fe088d9cfd0 -- thread:0x7fe088dcf3a0
    11.125 LOGOUT
    
    READ Jul 31 13:24:17.172 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 i7sm25209112wjg.42 - gsmtp
    
    WROTE Jul 31 13:24:17.172 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    AUTH LOGIN
    
    READ Jul 31 13:24:17.213 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    334 VXNlcm5hbWU6
    
    WROTE Jul 31 13:24:17.213 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    bWF0ZWRvYnJheUBnbWFpbC5jb20=
    
    READ Jul 31 13:24:17.250 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    334 UGFzc3dvcmQ6
    
    WROTE Jul 31 13:24:17.251 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    ********************************
    
    READ Jul 31 13:24:17.682 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    534-5.7.9 Application-specific password required. Learn more at
    534 5.7.9  https://support.google.com/accounts/answer/185833 i7sm25209112wjg.42 - gsmtp
    
    WROTE Jul 31 13:24:17.683 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fe0892cd9e0 -- thread:0x7fe085e7e5d0
    QUIT
    

    Don't know if that helps... Thanks for taking the time with this!
     
  22. MC6800 macrumors 6502

    Joined:
    Jun 29, 2016
    #22
    That's useful output-- from the second-to-last line in both logs, the Google site says it needs a correct app password, and to get more information from https://support.google.com/accounts/answer/185833
     
  23. baryon thread starter macrumors 68040

    baryon

    Joined:
    Oct 3, 2009
    #23
    Thanks! I now assigned an app-specific password to Mail, and it seems to have accepted it, but I still have problems. The exclamation marks next to Inbox still pop up eventually, and here is what Connection Doctor has to say now about the IMAP connection (SMTP seems fine now):

    Code:
    INITIATING CONNECTION Jul 31 20:42:53.594 host:smtp.gmail.com -- port:587 -- socket:0x0 -- thread:0x7fccf066e3c0
    
    CONNECTED Jul 31 20:42:53.652 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    
    READ Jul 31 20:42:53.692 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    220 smtp.gmail.com ESMTP a203sm14532138wma.0 - gsmtp
    
    WROTE Jul 31 20:42:53.703 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    EHLO [192.168.1.66]
    
    READ Jul 31 20:42:53.744 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    250-smtp.gmail.com at your service, [78.92.199.183]
    250-SIZE 35882577
    250-8BITMIME
    250-STARTTLS
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Jul 31 20:42:53.745 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    STARTTLS
    
    READ Jul 31 20:42:53.784 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    220 2.0.0 Ready to start TLS
    
    WROTE Jul 31 20:42:53.825 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    EHLO [192.168.1.66]
    
    READ Jul 31 20:42:53.944 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    250-smtp.gmail.com at your service, [78.92.199.183]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Jul 31 20:42:53.946 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    AUTH PLAIN  (*** 80 bytes hidden ***)
    
    READ Jul 31 20:42:54.101 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    235 2.7.0 Accepted
    
    WROTE Jul 31 20:42:54.101 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf08dadd0 -- thread:0x7fccf066e3c0
    QUIT
    
    It just spins and spins but never resolves with an error. I guess it just times out eventually.
     
  24. MC6800 macrumors 6502

    Joined:
    Jun 29, 2016
    #24
    Curiously, the output above appears to be for the SMTP connection ("host:smtp.gmail.com").
     
  25. baryon thread starter macrumors 68040

    baryon

    Joined:
    Oct 3, 2009
    #25
    I managed to catch it again, this seems to have more IMAP related stuff in it (there's no way to clear the log so it's hard to say which connection it happens to dump into it):

    Code:
    265 OK Success
    
    WROTE Aug 02 08:32:46.316 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf0d9cb60
    9.265 SELECT INBOX (CONDSTORE)
    
    WROTE Aug 02 08:32:46.396 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcceb72c2c0 -- thread:0x7fcced401bc0
    EHLO [192.168.1.66]
    
    READ Aug 02 08:32:46.519 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcceb72c2c0 -- thread:0x7fcced401bc0
    250-BLU436-SMTP74.smtp.hotmail.com Hello [188.36.172.207]
    250-TURN
    250-SIZE 41943040
    250-ETRN
    250-PIPELINING
    250-DSN
    250-ENHANCEDSTATUSCODES
    250-8bitmime
    250-BINARYMIME
    250-CHUNKING
    250-VRFY
    250-AUTH LOGIN PLAIN XOAUTH2
    250 OK
    
    WROTE Aug 02 08:32:46.520 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcceb72c2c0 -- thread:0x7fcced401bc0
    AUTH PLAIN  (*** 68 bytes hidden ***)
    
    WROTE Aug 02 08:32:46.544 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fcced14e710 -- thread:0x7fccf19d18d0
    EHLO [192.168.1.66]
    
    READ Aug 02 08:32:46.560 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf0d9cb60
    * FLAGS (\Answered \Flagged \Draft \Deleted \Seen $Forwarded $Junk $MailFlagBit0 $MailFlagBit1 $MailFlagBit2 $NotJunk $NotPhishing $Phishing JunkRecorded NotJunk)
    * OK [PERMANENTFLAGS (\Answered \Flagged \Draft \Deleted \Seen $Forwarded $Junk $MailFlagBit0 $MailFlagBit1 $MailFlagBit2 $NotJunk $NotPhishing $Phishing JunkRecorded NotJunk \*)] Flags permitted.
    * OK [UIDVALIDITY 606784099] UIDs valid.
    * 8341 EXISTS
    * 0 RECENT
    * OK [UIDNEXT 12554] Predicted next UID.
    * OK [HIGHESTMODSEQ 2048931]
    9.265 OK [R
    READ Aug 02 08:32:46.561 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf0d9cb60
    EAD-WRITE] INBOX selected. (Success)
    
    WROTE Aug 02 08:32:46.561 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf0d9cb60
    10.265 IDLE
    
    READ Aug 02 08:32:46.671 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf0d9cb60
    + idling
    
    WROTE Aug 02 08:32:46.672 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced28bc10
    DONE
    
    READ Aug 02 08:32:46.676 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fcced14e710 -- thread:0x7fccf19d18d0
    250-st11p01im-asmtp001.mac.com
    250-8BITMIME
    250-PIPELINING
    250-CHUNKING
    250-DSN
    250-ENHANCEDSTATUSCODES
    250-EXPN
    250-HELP
    250-XADR
    250-XSTA
    250-XCIR
    250-XGEN
    250-XLOOP 39E9E360E2A78188DBDBCDD9BD09E980
    250-AUTH PLAIN LOGIN ATOKEN
    250-AUTH=LOGIN PLAIN
    250-NO-SOLICITING
    250 SIZE 28311552
    
    WROTE Aug 02 08:32:46.676 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fcced14e710 -- thread:0x7fccf19d18d0
    AUTH ATOKEN  (*** 80 bytes hidden ***)
    
    READ Aug 02 08:32:46.815 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcceb72c2c0 -- thread:0x7fcced401bc0
    235 2.7.0 Authentication succeeded
    
    WROTE Aug 02 08:32:46.816 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcceb72c2c0 -- thread:0x7fcced401bc0
    QUIT
    
    READ Aug 02 08:32:46.909 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced28bc10
    10.265 OK IDLE terminated (Success)
    
    WROTE Aug 02 08:32:46.909 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced28bc10
    11.265 UID FETCH 1:12553 (FLAGS UID) (CHANGEDSINCE 2048908)
    
    READ Aug 02 08:32:46.963 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fcced14e710 -- thread:0x7fccf19d18d0
    235 2.7.0 ATOKEN authentication successful.
    
    WROTE Aug 02 08:32:46.963 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fcced14e710 -- thread:0x7fccf19d18d0
    QUIT
    
    READ Aug 02 08:32:47.088 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced28bc10
    11.265 OK Success
    
    WROTE Aug 02 08:32:47.091 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced401bc0
    12.265 LSUB "" *
    
    READ Aug 02 08:32:47.198 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced401bc0
    * LSUB (\HasNoChildren) "/" "Apple Mail To Do"
    * LSUB (\HasNoChildren) "/" "INBOX"
    * LSUB (\HasNoChildren) "/" "Notes"
    * LSUB (
    READ Aug 02 08:32:47.199 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced401bc0
    \HasChildren \Noselect) "/" "[Gmail]"
    * LSUB (\Drafts \HasNoChildren) "/" "[Gmail]/Drafts"
    * LSUB (\HasNoChildren \Sent) "/" "[Gmail]/Sent Mail"
    * LSUB (\HasNoChildren \Junk) "/" "[Gmail]/Spam"
    * LSUB (\HasNoChildren \Trash) "/" "[Gmail]/Trash"
    12.265 OK Success
    
    WROTE Aug 02 08:32:47.200 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced28bc10
    13.265 IDLE
    
    READ Aug 02 08:32:47.311 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced28bc10
    + idling
    
    WROTE Aug 02 08:32:47.311 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced333c10
    DONE
    
    READ Aug 02 08:32:47.419 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced333c10
    13.265 OK IDLE terminated (Success)
    
    WROTE Aug 02 08:32:47.419 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced333c10
    14.265 LIST "" *
    
    READ Aug 02 08:32:47.528 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced333c10
    * LIST (\HasNoChildren) "/" "Apple Mail To Do"
    * LIST (\HasNoChildren) "/" "INBOX"
    * LIST (\HasNoChildren) "/" "Notes"
    * LIST (
    READ Aug 02 08:32:47.529 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced333c10
    \HasChildren \Noselect) "/" "[Gmail]"
    * LIST (\Drafts \HasNoChildren) "/" "[Gmail]/Drafts"
    * LIST (\HasNoChildren \Sent) "/" "[Gmail]/Sent Mail"
    * LIST (\HasNoChildren \Junk) "/" "[Gmail]/Spam"
    * LIST (\HasNoChildren \Trash) "/" "[Gmail]/Trash"
    14.265 OK Success
    
    WROTE Aug 02 08:32:47.530 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced401bc0
    15.265 IDLE
    
    READ Aug 02 08:32:47.641 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced401bc0
    + idling
    
    INITIATING CONNECTION Aug 02 09:03:07.365 host:smtp.gmail.com -- port:587 -- socket:0x0 -- thread:0x7fccf2994d80
    
    INITIATING CONNECTION Aug 02 09:03:07.365 host:p01-smtp.mail.me.com -- port:587 -- socket:0x0 -- thread:0x7fcced3273b0
    
    INITIATING CONNECTION Aug 02 09:03:07.365 host:smtp-mail.outlook.com -- port:587 -- socket:0x0 -- thread:0x7fcced3a2d30
    
    INITIATING CONNECTION Aug 02 09:03:07.365 host:imap.gmail.com -- port:993 -- socket:0x0 -- thread:0x7fccf0510350
    
    WROTE Aug 02 09:03:07.366 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf08b4690
    DONE
    
    CONNECTED Aug 02 09:03:07.440 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    
    READ Aug 02 09:03:07.477 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf08b4690
    15.265 OK IDLE terminated (Success)
    
    WROTE Aug 02 09:03:07.477 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf08b4690
    16.265 NOOP
    
    CONNECTED Aug 02 09:03:07.525 [kCFStreamSocketSecurityLevelNone] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    
    READ Aug 02 09:03:07.561 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    220 smtp.gmail.com ESMTP v134sm20520906wmf.10 - gsmtp
    
    CONNECTED Aug 02 09:03:07.562 [kCFStreamSocketSecurityLevelNone] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    
    WROTE Aug 02 09:03:07.572 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    EHLO [192.168.1.66]
    
    READ Aug 02 09:03:07.600 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf08b4690
    16.265 OK Success
    
    CONNECTED Aug 02 09:03:07.608 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    
    READ Aug 02 09:03:07.608 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    * OK Gimap ready for requests from 188.36.172.207 tc2mb170328298wjb
    
    WROTE Aug 02 09:03:07.608 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    1.269 CAPABILITY
    
    READ Aug 02 09:03:07.614 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    250-smtp.gmail.com at your service, [188.36.172.207]
    250-SIZE 35882577
    250-8BITMIME
    250-STARTTLS
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Aug 02 09:03:07.614 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    STARTTLS
    
    READ Aug 02 09:03:07.648 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH2 AUTH=PLAIN AUTH=PLAIN-CLIENTTOKEN AUTH=OAUTHBEARER AUTH=XOAUTH
    1.269 OK Thats all she wrote! tc2mb170328298wjb
    
    READ Aug 02 09:03:07.649 [kCFStreamSocketSecurityLevelNone] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    220 BLU436-SMTP164.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at  Tue, 2 Aug 2016 00:03:08 -0700
    
    WROTE Aug 02 09:03:07.649 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    2.269 ID ("name" "Mac OS X Mail" "version" "9.3 (3124)" "os" "Mac OS X" "os-version" "10.11.6 (15G31)" "vendor" "Apple Inc.")
    
    READ Aug 02 09:03:07.653 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    220 2.0.0 Ready to start TLS
    
    WROTE Aug 02 09:03:07.657 [kCFStreamSocketSecurityLevelNone] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    EHLO [192.168.1.66]
    
    READ Aug 02 09:03:07.703 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    * ID ("name" "GImap" "vendor" "Google, Inc." "support-url" "http://support.google.com/mail" "remote-host" "188.36.172.207" "connection-token" "tc2mb170328298wjb")
    2.269 OK Success tc2mb170328298wjb
    
    WROTE Aug 02 09:03:07.704 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    7.269 AUTHENTICATE PLAIN  (*** 80 bytes hidden ***)
    
    READ Aug 02 09:03:07.705 [kCFStreamSocketSecurityLevelNone] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    220 st11p01im-asmtp001.mac.com -- Server ESMTP (Oracle Communications Messaging Server 7.0.5.38.0 64bit (built Feb 26 2016))
    
    WROTE Aug 02 09:03:07.713 [kCFStreamSocketSecurityLevelNone] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    EHLO [192.168.1.66]
    
    READ Aug 02 09:03:07.785 [kCFStreamSocketSecurityLevelNone] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    250-BLU436-SMTP164.smtp.hotmail.com Hello [188.36.172.207]
    250-TURN
    250-SIZE 41943040
    250-ETRN
    250-PIPELINING
    250-DSN
    250-ENHANCEDSTATUSCODES
    250-8bitmime
    250-BINARYMIME
    250-CHUNKING
    250-VRFY
    250-TLS
    250-STARTTLS
    250 OK
    
    WROTE Aug 02 09:03:07.785 [kCFStreamSocketSecurityLevelNone] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    STARTTLS
    
    WROTE Aug 02 09:03:07.830 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    EHLO [192.168.1.66]
    
    READ Aug 02 09:03:07.849 [kCFStreamSocketSecurityLevelNone] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    250-st11p01im-asmtp001.mac.com
    250-8BITMIME
    250-PIPELINING
    250-CHUNKING
    250-DSN
    250-ENHANCEDSTATUSCODES
    250-EXPN
    250-HELP
    250-XADR
    250-XSTA
    250-XCIR
    250-XGEN
    250-XLOOP 39E9E360E2A78188DBDBCDD9BD09E980
    250-STARTTLS
    250-NO-SOLICITING
    250 SIZE 28311552
    
    WROTE Aug 02 09:03:07.849 [kCFStreamSocketSecurityLevelNone] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    STARTTLS
    
    READ Aug 02 09:03:07.869 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE ENABLE MOVE CONDSTORE ESEARCH UTF8=ACCEPT LIST-EXTENDED LIST-STATUS APPENDLIMIT=35882577
    7.269 OK redacted@gmail.com authenticated (Success)
    
    WROTE Aug 02 09:03:07.869 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    8.269 CAPABILITY
    
    READ Aug 02 09:03:07.872 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    250-smtp.gmail.com at your service, [188.36.172.207]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Aug 02 09:03:07.874 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    AUTH PLAIN  (*** 80 bytes hidden ***)
    
    READ Aug 02 09:03:07.909 [kCFStreamSocketSecurityLevelNone] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    220 2.0.0 SMTP server ready
    
    READ Aug 02 09:03:07.910 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE ENABLE MOVE CONDSTORE ESEARCH UTF8=ACCEPT LIST-EXTENDED LIST-STATUS APPENDLIMIT=35882577
    8.269 OK Success
    
    WROTE Aug 02 09:03:07.910 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fcceb55c3a0 -- thread:0x7fccf0510350
    9.269 LOGOUT
    
    READ Aug 02 09:03:07.989 [kCFStreamSocketSecurityLevelNone] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    220 2.5.0 Go ahead with TLS negotiation.
    
    READ Aug 02 09:03:07.991 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    235 2.7.0 Accepted
    
    WROTE Aug 02 09:03:07.992 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fcceb71a870 -- thread:0x7fccf2994d80
    QUIT
    
    WROTE Aug 02 09:03:08.384 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    EHLO [192.168.1.66]
    
    WROTE Aug 02 09:03:08.456 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    EHLO [192.168.1.66]
    
    READ Aug 02 09:03:08.508 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    250-BLU436-SMTP164.smtp.hotmail.com Hello [188.36.172.207]
    250-TURN
    250-SIZE 41943040
    250-ETRN
    250-PIPELINING
    250-DSN
    250-ENHANCEDSTATUSCODES
    250-8bitmime
    250-BINARYMIME
    250-CHUNKING
    250-VRFY
    250-AUTH LOGIN PLAIN XOAUTH2
    250 OK
    
    WROTE Aug 02 09:03:08.509 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    AUTH PLAIN  (*** 68 bytes hidden ***)
    
    READ Aug 02 09:03:08.593 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    250-st11p01im-asmtp001.mac.com
    250-8BITMIME
    250-PIPELINING
    250-CHUNKING
    250-DSN
    250-ENHANCEDSTATUSCODES
    250-EXPN
    250-HELP
    250-XADR
    250-XSTA
    250-XCIR
    250-XGEN
    250-XLOOP 39E9E360E2A78188DBDBCDD9BD09E980
    250-AUTH PLAIN LOGIN ATOKEN
    250-AUTH=LOGIN PLAIN
    250-NO-SOLICITING
    250 SIZE 28311552
    
    WROTE Aug 02 09:03:08.594 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    AUTH ATOKEN  (*** 80 bytes hidden ***)
    
    READ Aug 02 09:03:08.809 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    235 2.7.0 Authentication succeeded
    
    WROTE Aug 02 09:03:08.809 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x7fcced39d5c0 -- thread:0x7fcced3a2d30
    QUIT
    
    READ Aug 02 09:03:08.907 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    235 2.7.0 ATOKEN authentication successful.
    
    WROTE Aug 02 09:03:08.907 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:p01-smtp.mail.me.com -- port:587 -- socket:0x7fccf0109150 -- thread:0x7fcced3273b0
    QUIT
    
    WROTE Aug 02 09:05:01.378 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced321790
    17.265 LSUB "" *
    
    READ Aug 02 09:05:01.492 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced321790
    * LSUB (\HasNoChildren) "/" "Apple Mail To Do"
    * LSUB (\HasNoChil
    READ Aug 02 09:05:01.494 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced321790
    dren) "/" "INBOX"
    * LSUB (\HasNoChildren) "/" "Notes"
    * LSUB (\HasChildren \Noselect) "/" "[Gmail]"
    * LSUB (\Drafts \HasNoChildren) "/" "[Gmail]/Drafts"
    * LSUB (\HasNoChildren \Sent) "/" "[Gmail]/Sent Mail"
    * LSUB (\HasNoChildren \Junk) "/" "[Gmail]/Spam"
    * LSUB (\HasNoChildren \Trash) "/" "[Gmail]/Trash"
    17.265 OK Success
    
    WROTE Aug 02 09:05:01.495 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf1e47840
    18.265 IDLE
    
    READ Aug 02 09:05:01.607 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fccf1e47840
    + idling
    
    WROTE Aug 02 09:05:01.607 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced571620
    DONE
    
    READ Aug 02 09:05:01.716 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced571620
    18.265 OK IDLE terminated (Success)
    
    WROTE Aug 02 09:05:01.716 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced571620
    19.265 LIST "" *
    
    READ Aug 02 09:05:01.826 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced571620
    * LIST (\HasNoChildren) "/" "Apple Mail To Do"
    * LIST (\HasNoChil
    READ Aug 02 09:05:01.828 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced571620
    dren) "/" "INBOX"
    * LIST (\HasNoChildren) "/" "Notes"
    * LIST (\HasChildren \Noselect) "/" "[Gmail]"
    * LIST (\Drafts \HasNoChildren) "/" "[Gmail]/Drafts"
    * LIST (\HasNoChildren \Sent) "/" "[Gmail]/Sent Mail"
    * LIST (\HasNoChildren \Junk) "/" "[Gmail]/Spam"
    * LIST (\HasNoChildren \Trash) "/" "[Gmail]/Trash"
    19.265 OK Success
    
    WROTE Aug 02 09:05:01.829 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced571620
    20.265 IDLE
    
    READ Aug 02 09:05:01.938 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x7fccf2a137e0 -- thread:0x7fcced571620
    + idling
    
    INITIATING CONNECTION Aug 02 10:15:17.998 host:imap.gmail.com -- port:993 -- socket:0x0 -- thread:0x7fccf0141460
    
    INITIATING CONNECTION Aug 02 10:15:54.414 host:imap.gmail.com -- port:993 -- socket:0x0 -- thread:0x7fccf0141460
    
    INITIATING CONNECTION Aug 02 10:29:54.917 host:imap.gmail.com -- port:993 -- socket:0x0 -- thread:0x7fccf1d56590
    
    INITIATING CONNECTION Aug 02 10:30:14.407 host:imap.gmail.com -- port:993 -- socket:0x0 -- thread:0x7fccf0e1fcd0
    
    INITIATING CONNECTION Aug 02 10:30:14.408 host:smtp.gmail.com -- port:587 -- socket:0x0 -- thread:0x7fccf0061f20
    
    CONNECTED Aug 02 10:30:14.472 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    
    READ Aug 02 10:30:14.532 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    220 smtp.gmail.com ESMTP us9sm1390924wjb.43 - gsmtp
    
    WROTE Aug 02 10:30:14.565 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    EHLO [192.168.1.66]
    
    READ Aug 02 10:30:14.608 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    250-smtp.gmail.com at your service, [188.36.172.207]
    250-SIZE 35882577
    250-8BITMIME
    250-STARTTLS
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Aug 02 10:30:14.608 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    STARTTLS
    
    READ Aug 02 10:30:14.648 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    220 2.0.0 Ready to start TLS
    
    WROTE Aug 02 10:30:14.817 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    EHLO [192.168.1.66]
    
    READ Aug 02 10:30:14.858 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    250-smtp.gmail.com at your service, [188.36.172.207]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
    250-ENHANCEDSTATUSCODES
    250-PIPELINING
    250-CHUNKING
    250 SMTPUTF8
    
    WROTE Aug 02 10:30:14.860 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    AUTH PLAIN  (*** 80 bytes hidden ***)
    
    READ Aug 02 10:30:14.987 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    235 2.7.0 Accepted
    
    WROTE Aug 02 10:30:14.987 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x7fccf0c54ff0 -- thread:0x7fccf0061f20
    QUIT
    
    INITIATING CONNECTION Aug 02 10:30:29.467 host:imap.gmail.com -- port:993 -- socket:0x0 -- thread:0x7fccf1d56590
    
     

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