Connection failures with GMail in Mail 6.0

I am also still having this problem with Mac Mail 6.1 on Mountain Lion. I can receive messages and gmail sends just fine from the web app, my iPhone, and iPad, but not Mac Mail. I get the same "the sender adress xxx@gmail.com was rejected by the server smtp.gmail.com.

I do not have 2-step verification turned on in Gmail.

Thank you!

I found a solution!! At least in regards to Gmail not connecting to anything Apple related.

Instead of turning off the 2-step verification, you can click on a link right below that says "Problems with your phone, email, or other apps?" and it'll lead you through how to create an "application-specific password." Basically, when you try to sign in to your gmail app on your iPhone/iPod or link your gmail account to your Apple Mail account, you can't connect because it doesn't ask for a verification code -- only your username and password. In other words, it isn't asking for the other half of your password.

Everything is explained really well if you go to Gmail/Settings/Accounts and Import/Other Google Account Settings/Security/2-Step Verification Edit/...retype your password.../Problems with your phone, emails, or other apps?/ and FINALLY, Authorizing applications and site passages. Before clicking on the last link, you might want to read part of the article, just so you have an idea of why you had to go through a jillion steps and how this final step is going to help.

So, by creating an application-specific password, you get to by-pass the two-step verification process, but you still get to keep the two-step for your actual email (i.e.: you still have the added protection that gmail is trying to provide, but without the extra steps for your other gmail links...I hope that made sense.)

For the first time in months I'm finally able to have Gmail on my phone and link all my emails together in my Apple mailbox 🙂

I found a solution!! At least in regards to Gmail not connecting to anything Apple related.

Instead of turning off the 2-step verification, you can click on a link right below that says "Problems with your phone, email, or other apps?" and it'll lead you through how to create an "application-specific password." Basically, when you try to sign in to your gmail app on your iPhone/iPod or link your gmail account to your Apple Mail account, you can't connect because it doesn't ask for a verification code -- only your username and password. In other words, it isn't asking for the other half of your password.

Everything is explained really well if you go to Gmail/Settings/Accounts and Import/Other Google Account Settings/Security/2-Step Verification Edit/...retype your password.../Problems with your phone, emails, or other apps?/ and FINALLY, Authorizing applications and site passages. Before clicking on the last link, you might want to read part of the article, just so you have an idea of why you had to go through a jillion steps and how this final step is going to help.

So, by creating an application-specific password, you get to by-pass the two-step verification process, but you still get to keep the two-step for your actual email (i.e.: you still have the added protection that gmail is trying to provide, but without the extra steps for your other gmail links...I hope that made sense.)

For the first time in months I'm finally able to have Gmail on my phone and link all my emails together in my Apple mailbox 🙂

I hope this helps!!

This applies to all SMTP issues. There appears to be a bug in Apple Mail (version 4.2-6.2). You can update your account information in 2 places:

1. Going to Mail >> Preferences >> Accounts and doing it there or....

2. When the connection to your SMTP server does not work you can 'edit' the SMTP list.

THE PROBLEM:

The 2 do not always stay in synch. It appears that changing one does not change both (issue with saving I suspect). I will post the problem to apple, but until then when you are making changes to get the smtp setting to work make sure both settings are the same.

If not, you could obviously do the 'correct' thing, get an erroneous failure, move on and be lost for hours. Based on the amount of traffic out here about SMTP issues, I would suspect that occurs to others frequently.

I've never set 2-step verification and I get this error " The sender address xxxxxt@gmail.com was rejected by the server smtp.gmail.com "

I followed advice in various forums: deactivated accounts both on mac and iPhone, set to get mail every 15 min, changed password and cleared CAPTCHA. In fact password is not the issue, the SMTP server does a rejection for other reasons and only when the request comes from the mac (works fine from iPhone).

Apple please HELP!

Alloceki,

Sorry if this is repeat or not, but I have gmail working forom multiple OS configs. Please try these settings:

Use custom port 465

Use SSL

Use Password Auth.

I want to stess that these setting need to be in the 'edited SMTP list'. When I pull up my gmail account - on the advanved tab it says something different then when I drop down in the general tab for SMTP and choose 'edit SMTP list'.

The settings in the SMTP list trump anything in the advanced tab....I know one should read from the other but it's a but in mail,,,,see my previous posts.

I just changed the setting - had it fail and changed them back to those listed above and it worked to gmail from 2 different OS versions.

Hope this solves it for you.

Wow, that worked! So mysterious that this issues has so many solutions that work for some and not for others.

I hope it does keep working, these mail client / Gmail problems seem to have been going on for years.

Thank you!

Well none of the above suggestions work for me. I have OSX 10.8.2 and Apple Mail 6.2 (1499). I never had a problem until about 3 days ago. I haven't recently upgraded anything, at least not knowingly, unless my MacBook did it of its own accord when I wasn't in front of it. Now I have continual connection problems with Apple Mail and my GMail accounts, another IMAP mail server and even with Apple's own iCloud mail server. As set out in postings above when Apple Mail starts it's fine, it downloads mails and then seems to run OK for a while but will, after some time, lose the connection to the various mail servers. Reasons given are either along the lines of login failed verify that user name and password are correct (they are) or, check network connection (its fine) and that you netered the correct information (its in the key chain and is correct) also verify the server supports SSL.

None of the suggestions above have worked. I don't use Google's 2 step verification and its disabled on those accounts anyway. I've changed port numbers, makes no difference. The fact that its the same problem with my iCloud mail account makes me think its not a Google issue but an Apple Mail issue. Unless someone has any bright suggestions I guess I'll have to keep restarting Apple Mail until Apple provide a fix.

By the way, mail via my iPhone is absolutely fine.

Any and all suggestions gladly received.

What worked for me was getting a special double authentication password generated by gmail and including that in both the SMTP and IMAP password fields instead of my gmail password.

I am running Mail 6.2 and recently ran into an issue where I could receive mail, but could not send from Mail. I also have device specific passwords turned on in Gmail. Turns out that this password got out of synch somehow and all I needed to do is reset the device specific password in Gmail. To do this:

1) Close out of Mac Mail

2) In Gmail: Go into Accounts > Manage security > Review permissions (Under Connected applications and sites)

3) At the bottom of the screen, "Revoke" the application-specific password for MacMail

4) Generate a new application-specific password for MacMail (COPY TO YOUR CLIPBOARD)

5) Go into "System Preferences" on your Mac

6) Go to "Mail, Contacts & Calendars"

7) Select your Gmail account > Click "Details…"

8) Enter your new Gmail password

9) Close System Preferences

10) Open Mac Mail

11) Go to Mail > Preferences

12) Look at the accounts Tab to ensure password are entered in both incoming and outgoing mail slots. NOTE: The "Outgoing Mail Server (SMTP):" line for me first said "None" If this is the case, you will need to click that drop down, Select "Edit SMTP Server list" and enter in your new password again in the sub dialog box.

Hope this can help someone else.

Thanks Mostew,

I had exactly the same problem.

I signed up for 2 step authentication, followed your steps and it all worked well.

Cheers,

Pete

Ever since I signed up for gmail 2-factor verification, I've had trouble with my Mac emails. I'd get an application specific password, enter it in the appropriate places and everything would work (I could receive and send emails using my gmail account). But after I would come back a few weeks or months later, I would no longer be able to send emails. Normally I just use gmail via a browser, but every now and then I need to send off an email via the Mac mail app (like if I want to share an iPhoto pic via email). At least 4 times now (weeks or months apart) I have found my Mac unable to send mail messages to my smtp-gmail.com server. So each time I had to generate a new gmail application-specific password and enter that as the outgoing maiil server (SMTP) password in my Mac's mail account preferences. So then things would seem to be fixed, but the trouble would always come back a few weeks or months later.

I'm trying some of the suggestions on this page. I think the suggestion by bravedawg (to update the password via 2 different methods) might have a good chance of working, so I'm trying that. What is curious is that things are working now. If things go as before, in a couple of months I will be unable to send emails out. How and when do things go awry? Maybe I need to make sure I use the mail app regularly (instead of every few weeks as I do now) so that I can correlate some other activity with causing this problem.

Step 12 was the kicker for me. Thank you Mostew.

Hi,

My email on my iPad with Imap settings of Gmail and the Settings on the iPad are not working right because before it was working right with imap connecting to gmail email on my iPad with the Apple Mail app. I have an error that keeps coming up every time I try to get it right it doesn't work. So what am I doing wrong cause I really want to get the settings right on the gmail website and the settings on my iPad that I'm doing wrong! Thanks

P.S. I hope I explained it enough if not let me know and I will try more! But I think I got it right!