Mail 5.0 and Google Apps - Help Please!

Discussion in 'Mac OS X Lion (10.7)' started by anon2828, Jul 25, 2011.

  1. anon2828 macrumors newbie

    Joined:
    Feb 4, 2008
    #1
    After doing some searches (outside of MacRumors) it appears that others are having the same problem:

    IMAP setup for Google Apps accounts is not working properly.

    Incoming mail works ok, but when sending it fails.

    As you can imagine, this is a big issue.

    Worse yet is if you have multiple gmail accounts (many do with a personal gmail account and a business/school Google Apps account) - If you attempt to send via the Google Apps account it fails and falls back to the personal account - thus your sent mail for your Google Apps account appears to come from your personal Gmail account - not good.

    It appears that the imap side of things (incoming) is ok, but the smtp side of things is messed up.

    Anyone have any ideas or know if this is a Apple Mail 5.0 issue or a Google Apps issue - or both?

    The above setup works just fine on iPhone, iPad and Windows using Outlook...

    Help appreciated.
     
  2. Freyqq macrumors 68040

    Joined:
    Dec 13, 2004
    #2
    make sure the smtp server, ports, etc are correct
     
  3. WizardHunt macrumors 68000

    WizardHunt

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    May 11, 2007
    Location:
    Las Vegas, Nevada USA
    #3
    And the ports you are speaking of are the defaults ones, 25, 587, and 465?
    Mine are checked off and still will not send out. Is there a way to check apple mail servers to see if they are operational?
     
  4. anon2828 thread starter macrumors newbie

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    Feb 4, 2008
    #4
    Yup - all of the ports and settings are correct. Even verified this with the Google Apps Enterprise support folks.

    Seems that Google Apps gmail and Apple Mail 5 don't like eachother - which is going to be a huge issue for our small business - and potentially force us back to the hated MS Outlook...

    Anyone else have any other ideas?
     
  5. gentlefury macrumors 68030

    Joined:
    Jul 21, 2011
    Location:
    Los Angeles, CA
    #5
    It works when it wants to. I have some days where its perfectly fine, other days it gives me an error that my password is wrong.....but its not a lion problem because my iPhone and iPad got the same error at the same time...so its a problem on Googles side.
     
  6. mrapplegate macrumors 68030

    Joined:
    Feb 26, 2011
    Location:
    Cincinnati, OH
    #6
    Port 25 is not used for SSL.


    Incoming Mail (IMAP) Server - requires SSL: imap.gmail.com
    Use SSL: Yes
    Port: 993
    Outgoing Mail (SMTP) Server - requires TLS: smtp.gmail.com (use authentication)
    Use Authentication: Yes
    Use STARTTLS: Yes (some clients call this SSL)
    Port: 465 or 587
    Account Name: your full email address (including @gmail.com) Google Apps users, please enter username@your_domain.com
    Email Address: your full Gmail email address (username@gmail.com) Google Apps users, please enter username@your_domain.com
    Password: your Gmail password


    Apple has nothing to do with Gmails servers, so no need to check with them unless you use me.com.
     
  7. superfula macrumors 6502

    Joined:
    Mar 17, 2002
    #7
    Are the issues happening on accounts that were added to Mail in Lion or were they added before you upgraded to Lion? Or both?

    I know this isn't much help, but I've got a Google Apps email and two normal gmail accounts in Mail 5. I have yet to see any issues. Course they were added under SL. When I get home I'll try adding a few accounts now that I have Lion running and see what happens.
     
  8. WizardHunt macrumors 68000

    WizardHunt

    Joined:
    May 11, 2007
    Location:
    Las Vegas, Nevada USA
    #8
    I use MobileMe mostly so what ports should I be using to set this up. I wish Lion would not have changed these as they were set up fine when I was using Snow Leopard and I had no trouble at all.

    So basically what I am asking is this , what port should be configured for my outgoing mail for my MobileMe account? Also should I set Use Authentication: Yes on my MobileMe account?
     
  9. mrapplegate macrumors 68030

    Joined:
    Feb 26, 2011
    Location:
    Cincinnati, OH
    #9
    I'm confused. What is the problem then? Your post was about IMAP gmail accounts. For mobile me mail support try, http://www.apple.com/support/mobileme/

    Incoming Mail Server: mail.me.com
    Outgoing Mail Server: smtp.me.com (make sure to use authentication with your outgoing mail server)
    Outgoing Mail Server: smtp.me.com (for either me.com or mac.com addresses)
    Server port: 587 or 25 (some ISPs may block port 25)
    "Use Secure Sockets Layer (SSL)" should be checked (enabled)
    Authentication: Password
    User Name: Your MobileMe member name (without "@me.com" or "@mac.com")
    Password: Your MobileMe password

    The above information was learned from the below KB articles.
    http://support.apple.com/kb/ht2296
    http://support.apple.com/kb/ts1152
     
  10. superfula macrumors 6502

    Joined:
    Mar 17, 2002
    #10
    He's not the op, who is having issues with google mail accounts.
    WizardHunt seems to be having issues sending from a mobileme account. Two different people posting two different problems in one topic is no good.

    anon2828...I just added a normal gmail as well as a google apps account to Mail in Lion. Neither had any issues sending emails. I'm guessing there's something amiss with your SMTP settings. Could you post some screenshots of your IMAP and SMTP settings?
     
  11. mrapplegate macrumors 68030

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    Feb 26, 2011
    Location:
    Cincinnati, OH
    #11
    Oops, sometimes I need to read better . Thanks :)
     
  12. WizardHunt macrumors 68000

    WizardHunt

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    May 11, 2007
    Location:
    Las Vegas, Nevada USA
    #12
    My Bad, I did not realize. I am sorry. I will not post any further about this subject in this area.
     
  13. mrapplegate macrumors 68030

    Joined:
    Feb 26, 2011
    Location:
    Cincinnati, OH
    #13
    I'm sure the OP did not mind. I was just in the Gmail mindset and was thrown off about a jump to me.com question. Easily distracted/confused I guess :)
     
  14. anon2828 thread starter macrumors newbie

    Joined:
    Feb 4, 2008
    #14
    Thanks for the responses so far - most appreciated.

    To clarify a bit more - I can send from Mail 5 - HOWEVER - with the two Google accounts setup (one normal public gmail and the other Google Apps gmail) - when you send from the Google Apps account it falls back to send from the normal gmail account since it can't connect via SMTP to Google Apps. Worse is that you don't notice the problem and you end up sending business email from your personal gmail account...

    Summary:

    2 Gmail accounts - 1 normal public gmail (we'll call the just Gmail here) and 1 Google Apps gmail (let's just call this Google Apps)

    Receive via IMAP:
    Gmail ---> Works fine
    Google Apps ---> Works fine

    Send IMAP (actually SMTP)
    Gmail ---> Works fine (send properly with the from address reflecting Gmail account)
    Google Apps ---> Will send, but does not use the from address reflecting the Google Apps account - ends up using the from address of the Gmail account.

    This can be further clarified by removing the Gmail account (leaving only the Google Apps account) at which time you can't send at all since Mail 5 is having some type of issue connecting via SMTP to Google Apps...

    Screen shots to follow - again thanks for the help!
     
  15. mrapplegate macrumors 68030

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    Feb 26, 2011
    Location:
    Cincinnati, OH
    #15
    For the account that send mail as another address.
    do you have in mail to only send with that server?
    Also check the gmail web interface. You can choose to send mail from another email address, and it will show as being sent from that email.
    Under Settings, Accounts, Send Mail As.
     

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  16. anon2828 thread starter macrumors newbie

    Joined:
    Feb 4, 2008
    #16
    Yup - I definitely have that box checked.

    Even went through the advanced SMTP settings and everything seems to be configured correctly.

    I am curious to see the other posters results when he looks at what email address things were being sent from...

    Thanks for the help!

    I also have a case open with Google Enterprise support - they are unfortunately a bit clueless...I guess that is what $50 per user per year buys you...
     
  17. mrapplegate macrumors 68030

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    Feb 26, 2011
    Location:
    Cincinnati, OH
    #17
    I was thinking that you had the setting. Check your Google Apps account and make sure you are not "sending as" your regular gmail account. Does that make sense? That would explain why Apple mail is sending them out as your regular gmail account even though you are using the google apps account as the sender. Pure guessing though. I have no clue as the POP and IMAP protocols are standard.
    I don't remember reading it, but did you just deleted the account and add it again?
     
  18. anon2828 thread starter macrumors newbie

    Joined:
    Feb 4, 2008
    #18
    Again - thanks - you guys are very helpful and it is appreciated...

    I don't have any setting in Google Apps gmail that would cause it to send from the Gmail account...I know what you are talking about.

    In testing, I downloaded a 30-day trial version of MS Outlook 2011 and it worked without any issues whatsoever. Gmail sent from Gmail address and Google Apps sent from the Google Apps address.

    I know that some would say, "OK - problem solved, use Outlook," but it really should work in Apple Mail 5 and I really don't want to pay for MS Office...

    By the way, Google Enterprise's official support this morning was, "sorry - OS X Lion has just been released and we don't officially support Apple Mail 5"

    Now onto Apple Support unless you guys can solve it first. Still interested to hear the results of the other posters testing...
     
  19. nutmac macrumors 68040

    Joined:
    Mar 30, 2004
    #19
    Just out of curiosity, why are you using IMAP instead of Exchange? I use Exchange for Google Apps and it works great on Lion Mail.
     
  20. anon2828 thread starter macrumors newbie

    Joined:
    Feb 4, 2008
    #20
    I can certainly attempt to set it up using the Exchange option as you've mentioned, but on all other mail clients (including Outlook), I've always used IMAP without any issues...

    I'll test and report back. Any other suggestions are welcomed.

    PS - lots of others are apparently having this same issue as it appears on the Google forums and Apple support forums...

    Thanks again.
     
  21. superfula macrumors 6502

    Joined:
    Mar 17, 2002
    #21
    Well, starting a new thread will probably get you help quicker and that is more specific to your issues.

    It'll also help with mrapplegate's sanity. ;)
     
  22. mrapplegate macrumors 68030

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    Feb 26, 2011
    Location:
    Cincinnati, OH
    #22
    I just need to work on my multitasking skills :D and obviously my reading comprehension skills.
     
  23. Zcott macrumors 68020

    Joined:
    Oct 18, 2009
    Location:
    Belfast, Ireland
    #23
    FWIW I have a Google Apps account and no issues with Mail. The account was setup automatically through Mail, Contacts & Calendars and worked fine first time.
     
  24. anon2828 thread starter macrumors newbie

    Joined:
    Feb 4, 2008
    #24
    OK - I did a TON of testing over the weekend.

    Again, thanks for all of the feedback and comments.

    Some observations and replies to those who commented above:


    1) Yes, you can get Mail 5 to work with Google Apps gmail. This really isn't the issue. It is when you have BOTH a Google Apps gmail and a regular gmail (name@gmail.com) account configured in Mail. All sent mail will default to the from address of the regular Gmail account even if all SMTP settings are proper (including sending mail from the proper account).


    2) Even isolating the issue and only setting up a Google Apps gmail account in Mail 5 is not working well. Yes you can receive, and send (from the correct Google Apps gmail from address - since there is only one account configured), but if you watch closely the sending through SMTP is VERY VERY SLOW and not altogether right. Some messages were taking forever to get sent.

    3) I tried every setting imaginable and all of those recommended above and by Google. (PS - I have resold Google Apps, so I am a bit familiar - just not as intimate with Apple Mail):

    imap.gmail.com - port 993 SSL
    smtp.gmail.com - port 587 SSL and TLS
    All proper login names and passwords used
    All proper send from information entered

    4) I ended up downloading the trial version of MS Outlook for Mac 2011. Did all the setup the same way, and...guess what...it works without any issues. So I have to conclude that Apple Mail 5 does not like (at least not right now) having to deal with a Google Apps gmail account and a regular Gmail account. It gets confused and sends through the regular Gmail account regardless of settings - not good. Like I've said before, this issue is posted on Google's forums and Apple's as well.

    For now I'll have to use Outlook for Mac 2011 until Apple can get the bugs out of Mail 5. I was looking forward to ditching everything having to do with MS and embracing the simplicity of all that is Mac, but alas, not for right now...
     
  25. DJLC macrumors 6502a

    DJLC

    Joined:
    Jul 17, 2005
    Location:
    Mooresville, NC
    #25
    FWIW, I have 5 Google Apps accounts and 1 regular Gmail account set up in Apple Mail. I set them up in Snow Lep, and all is well. I'm even able to send from an alias associated with one of the Apps accounts. In my SMTP settings, I'm using SSL + Password authentication rather than SSL + TLS, if that helps at all.
     

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