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My Mac's Mail program stopped sending & receiving mail???

crowe-t

crowe-t

macrumors 6502
Original poster
Feb 7, 2014
333
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Satellite Of Love
I have an older Mac Mini from 2009. I'm running Mac OS 10.6.8. I have some older programs that so I stayed with 10.6.8. Soon I'll be getting a new Mac but for now I'm staying with the older Mac OS.

Recently my Mac Mini stopped sending and receiving e-mails on the Mail program. I use AOL(Verizon) for my e-mail. I checked the settings and everything looks OK. I hadn't made any changes.

Could this be due to 10.6.8 or could there be another problem why I'm unable to send and receive mail on my Mac using the Mail program?
 
I think you'll first have to dig into the AOL/Verizon support to see if there's some security change that is mucking up the works. Many email providers have a setting or procedure for allowing "less secure apps" to access the servers.
 
You can't use a newer version of Apple Mail without upgrading your OS. But if it's an https problem, that's fixable via the link I posted above.
 
Wowfunhappy said:
You can't use a newer version of Apple Mail without upgrading your OS. But if it's an https problem, that's fixable via the link I posted above.
Click to expand...
I can load up AOL/Verizon's website in Safari. I don't think it's an https problem. 10.6.8 is just not supported anymore.
 
Wowfunhappy said:
You can't use a newer version of Apple Mail without upgrading your OS. But if it's an https problem, that's fixable via the link I posted above.
Click to expand...
I went to that link and ran Squid. Do I need to re-boot the Mac to make it work?

For some reason now Safari won't go to the Apple web site.
 
Wowfunhappy said:
You can't use a newer version of Apple Mail without upgrading your OS. But if it's an https problem, that's fixable via the link I posted above.
Click to expand...
I just re-booted and I still can't receive mail in the Mail program. Is there something else I have to do or enable?
 
Nope, that just means it wasn't an https problem. :( Sorry, it was worth a try.

I am surprised though, I wouldn't have expected AOL to just break like that. I wonder if it's possible to set up as a generic POP/IMAP account instead of going through AOL specifically...
 
Wowfunhappy said:
Nope, that just means it wasn't an https problem. :( Sorry, it was worth a try.

I am surprised though, I wouldn't have expected AOL to just break like that. I wonder if it's possible to set up as a generic POP/IMAP account instead of going through AOL specifically...
Click to expand...
I don't know how to do that.

Should I remove the Squid program or leave it on my computer?
 
I mean, I would leave it anyway on Snow Leopard. You'll probably notice that Wikipedia works again in the Dictionary app, for example.

I still wonder what's wrong... I did a little digging and it looks like AOL does indeed use IMAP. That's a standard—it really shouldn't change. Do any errors appear in the console when you try to get more mail?
 
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Wowfunhappy said:
I mean, I would leave it anyway on Snow Leopard. You'll probably notice that Wikipedia works again in the Dictionary app, for example.

I still wonder what's wrong... I did a little digging and it looks like AOL does indeed use IMAP. That's a standard—it really shouldn't change. Do any errors appear in the console when you try to get more mail?
Click to expand...
I get this.
 

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Wowfunhappy said:
I mean, I would leave it anyway on Snow Leopard. You'll probably notice that Wikipedia works again in the Dictionary app, for example.

I still wonder what's wrong... I did a little digging and it looks like AOL does indeed use IMAP. That's a standard—it really shouldn't change. Do any errors appear in the console when you try to get more mail?
Click to expand...
Here's what it says in Mail Connection Doctor.
 

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I was wondering about /Applications/Utilities/Console.app, which may provide more information. When you try to connect in Mail, do any errors appear in the console?
 
I don't have AOL, but I suspect that this is an issue with the encryption. For some incomprehensible reason, few e-mail providers today support older versions of SSL, let alone unencrypted access. You need to solve this with a proxy, similar to Wowfunhappy's Squid proxy, but using the program stunnel instead.

I'll leave some instructions on how to install and configure stunnel for this. Note that you need to install MacPorts before doing any of this. Also, be careful. Some UNIX experience is required. If you feel you're not up to the task, I think some version of Thunderbird would likely support both OS 10.6 and modern encryption.

(1) Install stunnel:

Code: 
sudo port install stunnel

(2) Edit /opt/local/etc/stunnel/stunnel.conf (as super-user):

Code: 
# Certificate/key is needed in server mode and optional in client mode
cert = /opt/local/etc/stunnel/stunnel.pem
key = /opt/local/etc/stunnel/stunnel.pem
foreground = yes

# Some performance tunings
socket = l:TCP_NODELAY=1
socket = r:TCP_NODELAY=1
#compression = rle

# Workaround for Eudora bug
options = DONT_INSERT_EMPTY_FRAGMENTS

# Some debugging stuff useful for troubleshooting
#debug = 7
#output = stunnel.log

# Use it for client mode
client = yes

# Service-level configuration

[imap]
accept = 143
connect = IMAP.YOURPROVIDER.COM:993

[smtp]
accept = 25
connect = SMTP.YOURPROVIDER.COM:587
protocol = smtp
protocolUsername = YOURUSERNAME
protocolPassword = YOURPASSWORD

(3) Ensure the configuration file is not world-readable:

Code: 
sudo chmod 600 /opt/local/etc/stunnel/stunnel.conf

(4) Create /Users/USERNAME/Library/LaunchAgents/org.macports.stunnel.plist:

Code: 
<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
    <key>Label</key>
    <string>org.macports.stunnel</string>
    <key>ProgramArguments</key>
    <array>
        <string>sudo</string>
        <string>/opt/local/bin/stunnel</string>
    </array>
    <key>RunAtLoad</key>
    <true/>
</dict>
</plist>

(5) Allow your user to run stunnel as super-user without password:

Code: 
echo 'YOURUSERNAME ALL=(ALL) NOPASSWD: /opt/local/bin/stunnel' | sudo tee -a /etc/sudoers

(6) Load stunnel launch agent:

Code: 
launchctl load ~/Library/LaunchAgents/org.macports.stunnel.plist


Now, you need to add a new account in Mail.app. Supply localhost as the IMAP and SMTP server. Enter your normal credentials. If you've done everything correctly (and I haven't forgotten anything in my instruction), you should be able to send and receive e-mail now.
 
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I try for days to get stunnel running with Applemail and OS 10.6. I use stunnel 5.59 running with OpenSSL 1.1.1k (build from the source). I experimented a lot with the settings but no success.

Stunnel starts without complains and when I send a mail, the connection seems to be established successfully (according to the stunnel protocol), but mail show a spinning wheel for about 10-15s and then gives up. The stunnel protocol shows for that action an "Unexpected socket close":

Code: 
2021.07.22 16:54:22 LOG7[0]: Service [strato-pop3] started
2021.07.22 16:54:22 LOG7[0]: Setting local socket options (FD=3)
2021.07.22 16:54:22 LOG7[0]: Option TCP_NODELAY set on local socket
2021.07.22 16:54:22 LOG5[0]: Service [strato-pop3] accepted connection from 127.0.0.1:49864
2021.07.22 16:54:22 LOG6[0]: s_connect: connecting 81.169.145.131:995
2021.07.22 16:54:22 LOG7[0]: s_connect: s_poll_wait 81.169.145.131:995: waiting 10 seconds
2021.07.22 16:54:22 LOG7[0]: FD=6 events=0x1 revents=0x0
2021.07.22 16:54:22 LOG7[0]: FD=13 events=0x5 revents=0x0
2021.07.22 16:54:22 LOG5[0]: s_connect: connected 81.169.145.131:995
2021.07.22 16:54:22 LOG5[0]: Service [strato-pop3] connected remote server from 192.168.17.130:49865
2021.07.22 16:54:22 LOG7[0]: Setting remote socket options (FD=13)
2021.07.22 16:54:22 LOG7[0]: Option TCP_NODELAY set on remote socket
2021.07.22 16:54:22 LOG7[0]: Remote descriptor (FD=13) initialized
2021.07.22 16:55:22 LOG3[0]: Unexpected socket close (s_read)
2021.07.22 16:55:22 LOG5[0]: Connection reset: 0 byte(s) sent to TLS, 0 byte(s) sent to socket
2021.07.22 16:55:22 LOG7[0]: Remote descriptor (FD=13) closed
2021.07.22 16:55:22 LOG7[0]: Local descriptor (FD=3) closed
2021.07.22 16:55:22 LOG7[0]: Service [strato-pop3] finished (0 left)
2021.07.22 16:55:22 LOG7[0]: str_stats: 1 block(s), 32 data byte(s), 90 control byte(s)
2021.07.22 16:55:22 LOG7[0]: str_stats: 32 byte(s) at network.c:735

Any ideas what could have went wrong?
Complete conf and log in the attachment
 

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Wowfunhappy said:
Someone with more experience with stunnel might be able to help, but I'd still recommend just using https://jonathanalland.com/legacy-mac-proxy.html instead.
Click to expand...
I gave that proxy a try, but out of the box it does not solve the problem. From the description of the proxy it seems only to take care of the https protocol. This may be useful for loading some external content once the mail connection is established.

My primary problem is the pop3, imap and smtp protocol, to get a connection to my email service provider at all. The email service provider dropped for these protocols the support of SSL and TLS less than TLS 1.2 for "security reasons".

It might be possible to solve that with the squid proxy too but, I think, for that its configuration would need to be extended.
 
I’m not an expert on mail protocols but I’m pretty sure POP, IMAP, and SMTP all operate over http/https.

Note that https, ssl, and tls are all basically the same thing in common usage.

Now, if your provider totally dropped POP and IMAP that would be an issue. But, do they not support exchange?
 
My provider did not drop pop or imap, he only rised the needed security level.
Wikipedia does not mention http/https anywhere in e.g. its imap article.
https, imap .... operate all over TLS. But TLS is not https ... I think.
 
Technically, https is the protocol that uses ssl/tls.

Let me put it this way—as the maker of that package, I would like to make mail work if at all possible.

To confirm—you tried it already (without stunnel, I don’t know if it would interfere) and it didn’t work? Anything in the console (again without stunnel)?
 
It would be great if you could extend the functionality of your proxy to cover also email :)

Yes I installed the proxy, but reading the instructions I already run in the problem how to configure email to use it. Applemail has no setting "use proxy" and in the sys-preferences network settings, proxy section there is nothing that looks like mail.

I tried it nevertheless (without stunnel running). The behaviour just did not change. The email account that needs TLS>=1.2 did not respond. My other email account that still works, was working as before. There are no console messages. If you know how to increase the verbosity of the apple mail messages, to get more output, please tell me.

I am willing to try out any suggestions you have.
 
...I'd totally forgotten the proxy didn't work for crowe-t earlier (in this very thread no less).

🤔

Okay, next question, is there anything from Squid?

Open a Terminal and run:

/Library/Squid/squid -k shutdown

And then after about 60 seconds, run:

/Library/Squid/squid -d 0

A lot of errors will appear immediately; you can ignore those.

Try to connect in Apple Mail, and tell me if anything new appears in the Terminal when you do. I basically want to know if Mail is using the proxy at all.
 
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I am currently not with the computer that runs on OS 10.6. I will try tomorrow.
 
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