Upgraded to Lion, now Apple Mail no longer sends via SMTP to GMAIL

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Upgraded to Lion, now Apple Mail no longer sends via SMTP to GMAIL

Greetings! First and foremost, THANK YOU for reading this discussion. I truly appreciate any and all assistance. Being one who likes to exhaust all resources before posting, I have literally spent that last 7 and a half hours reading pages and pages of threads here, on Google Forums along with finding other data across the net.

The problem started immediately upon the LION upgrade. Everything worked fine until the upgrade and then BOOM...no more Apple Mail sending to Gmail SMTP server. I can receive Gmail just fine, but no can send.When a message is sent, after a long while, an error message pops up stating that the SMTP server is "off line." Obviously it is timing out.

I have confirmed the settings in Preferences. I have cleaned the hard drive (running the internal First Aid app). I confirmed the password was correct in KeyChain. I have tried a lot of corrective methods as stated in the threads.

I have tried using different ports (25, 465, 587). I have set the connection from smtp.gmail.com to actual IP addresses including the following:

209.85.227.109

74.125.91.109

74.125.39.16

74.125.157.109

74.125.113.109

173.194.68.109

I tried it with and without TLS/SSL enabled.

With authentication and without.

I even tried to telnet from the Mac to smtp.gmail.com without success. (I can telnet from a Windows machine though...OUCH)

I am NOT running LION OS X server, just plain old LION OS 10.8.2 on my MacBrook Pro.

Thank you in advance for any and all courtesies extended. Looking to resume using Apple Mail with my Gmail account ASAP.

Sincerely,

MWG2

MacBook Pro (13-inch Mid 2010), OS X Mountain Lion (10.8.2)

Posted on Jan 19, 2013 7:31 PM

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Answer 1

Lanny

Level 6

13,183 points

Jan 19, 2013 8:36 PM in response to MWG2

Delete the GMail account from Mail and then add it back.

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Answer 2

Jan 19, 2013 11:50 PM in response to MWG2

I don't use Mail - I use Outlook - but I've no problem with my GMail account - I just use the smtp.gmail.com server on port 465, with SSL enabled and user name and password verification.

I just don't like Mail, which is why I use Outlook - way to many messages here form people who can connect one day and then - bam - no longer able to send and/or receive messages.

Good luck,

Clinton

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Answer 3

MWG2 Author

Level 1

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Jan 20, 2013 6:48 AM in response to Lanny

Thank you for your reply Lanny. I deleted the account, completely shut down the Mac, restarted, added Gmail and UNFORTUNATELY it is still doing the same thing! It can get mail, but can't send. It keeps 'timing out'. It says the smtp server is 'off line'. I ping the servers from another computer (Windows) and the servers are there.

Something in my MAC since I downloaded LION is preventing it from sending. Any ideas?

Thanks so much!

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Answer 4

Lanny

Level 6

13,183 points

Jan 20, 2013 7:10 AM in response to MWG2

Try deleting all of the SMTP entries under SMTP, then deleting the account and adding it back. Just quit Mail and restart it. You don't need to shut down the Mac.

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Answer 5

MWG2 Author

Level 1

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Jan 20, 2013 7:13 AM in response to Lanny

The challenge is when you delete the account and then add it back, the system automatically inserts the SMTP information.

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Answer 6

Lanny

Level 6

13,183 points

Jan 20, 2013 7:18 AM in response to MWG2

Yes, that's the idea. Sometimes that info can get corrupted after an OS upgrade.

I'm going to add a Gmail account to my Mail and will report back the SMTP settings that it installs by default.

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Answer 7

Lanny

Level 6

13,183 points

Jan 20, 2013 7:24 AM in response to MWG2

Okay, this is what I got, and I just sent myself a test message, and it worked.

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Answer 8

Lanny

Level 6

13,183 points

Jan 20, 2013 7:32 AM in response to MWG2

Now, note that after I delete the Gmail account the SMTP settings remain. That's why you need to delete them separately before adding the account back.

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Answer 9

MWG2 Author

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Jan 20, 2013 10:18 AM in response to Lanny

Thanks Lanny...tried it...still doesn't work. Called Apple Support...switched to Tier 2 support person Chris P. Was on the phone with him for 2 hours and 38 minutes...we tried everything under the sun...still can't get to smtp.gmail.com...can't even telnet to it from Mac. We did network testing too...he thought my router was blocking ports 25, 465 & 587 but the router wasn't. After exhausting every concievable MAC setting, trying a number or solutions, killing the account and re-installing multiple times, his conclusion is that there is a third party software "blocking" the send in gmail...ummmmm...makes no sense to me as everything worked perfectly until I upgraded to OS X. Hence his solution is for me to take my Mac to the Apple Store and have them look at it. My solution? Don't use mail on the Mac and keep using Mail on my Windows machine. I prefer Mac, but I have now spent over the last two days in excess of 10 hours on this problem...it's not supposed to be this difficult. Lesson Learned...if something's working, DON'T goof with it...Apple Mail under Snow Leopard worked perfectly...upgraded to Mt. LION (paid for it) and now I am really paying the price for doing that. 😢

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Answer 10

CT

Level 7

23,987 points

Jan 20, 2013 10:21 AM in response to MWG2

When you upgrade your OS, there is always a decent chance that something you've done in the past, e.g., some third party software, will come to haunt you.

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Answer 11

Lanny

Level 6

13,183 points

Jan 20, 2013 11:03 AM in response to MWG2

From the Gmail site:

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Answer 12

MWG2 Author

Level 1

0 points

Jan 20, 2013 3:52 PM in response to MWG2

Does anyone out there know of any utility, or trouble shooting steps on how I can determine what is blocking the SMTP from connecting with the Gmail SMTP server? NOTE: I can connect to the iCloud SMTP server without any problem whatsoever. It's only the Gmail SMTP server that is not connecting. I can't even telnet to any of the GMAIL SMTP servers from my Mac.

THANKS!!!!

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Answer 13

MWG2 Author

Level 1

0 points

Jan 20, 2013 4:01 PM in response to CT

The Apple Tech "thinks" that it is "pssible" third party software may be the culpret. As for me and my house...I think there is a setting in the LION OS that is hindering any connectivity to the Gmail SMTP servers. This all started when I upgraded to LION. Scratchin' my head...

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Answer 14

Feb 4, 2013 11:35 PM in response to MWG2

Hi MWG2,

If it's any consolation I just bought my new macbook air and have the same issue. from what I've been reading on the web it's definitely related to LION.

I will go to the Apple store soon (as much like yourself I have exhusted every possible solution out there) and if they fix it I will report back.

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Answer 15

MWG2 Author

Level 1

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Feb 6, 2013 4:02 PM in response to LetMyPeopleGo

Remember to BACK UP everything BEFORE you go to the Genius Bar. Then remind them to instruct you exactly what to restore in your Macbook Air. There are a few items that should NOT be restored or the problem will rear it's ugly, snarling Lion head again. Just so you know, everything works fine now...but...it took a complete re-build of the hard drive and reinstall of Mt. Lion. Then restored from the Back Up drive (except for a few items they told me NOT to restore). Best of luck! (The Genius Bar people are excellent.)

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