Apple Mail & Gmail SMTP Not Working

If you can log onto gmails website fine, try this

Delete the account in question (make sure your doing it from System Preferences and then goto

https://www.google.com/accounts/UnlockCaptcha

do that stuff and wait about 3 minutes.

Add the account again, and see what happends

Koda were you able to get this to work?

i'm not having problems with both my gmail accounts but one in particular. The one I use for work which i set up to reply from a different address.

Mail will add my signature, and i can see that i'm using the correct account. But it will reply from personal email. I made an appointemnt at Genuius bar today but couldn't convice the attendant the problem was with apple. She said it was with our work server. Explained to her once I receive the email it's out of that server and the problem is between mail and gmail..........

any way, looks like you are experienceing the same problem.

And yes, i've deleted the account numerous times to no avail.

Mail works fine from my iPhone and fine from Gmail directly......

Tried this, appears to have worked

- Mail Preferences

- Account Tab

- Select 'Edit SMTP Server List' from the Outgoing Mail Server: pop up

- In the edit screen, go to the Advanced Tab

- Enter your email account password and save.

Hi, i had the exact same problem after upgrading to 10.8.2. all my gmail accounts in my Apple Mail account suddenly stopped sending mail and it doesn't accept my password.

After an exhausting all options, i finally found a fix. The problem is most likely with gmail (or maybe apple too).

Google introduced a new security measure called 2-step verification which assigns a unique password PER application that uses gmail - which you are supposed to only enter once. Current settings for 2-Step Verfication is set at OFF. You can turn this ON by logging into your gmail via web and go to ACCOUNT SETTINGS under SECURITY.

I turned ON my 2-step verification followed the instructions and clicked on generate password for my APPLE MAIL and used that new password on my APPLE MAIL gmail password. Don't forget to change the password in the SMTP server as well.

I used the same password for my iOS Mail and it works too.

Everything started working again....I know it is a bit of an effort especially if you have multiple gmail accounts but anything that improves your online security is worth doing. Gmail said we only have to input the long passwords once - let's hope it's true.

I'm attaching a link on gmail's 2-step verifcation setup. Hope this helps! Cheers!

http://support.google.com/a/bin/answer.py?hl=en&answer=175197

This worked for me, too. I have a two-weeks old MacBook Pro 2.9 GHz Intel Core i7 with 10.8.3 and it has been very frustrating so far, with Mail telling me that Gmail's SMTP server was offline. The first week was fine then it got steadily worse, until this afternoon when I tried all of the fixes which I found here and in other places and nothing worked (closing and opening Mail, restarting MacBook, editing smtp server list, re-entering password, unchecking SSL authentication, unlocking captcha, you name it).

I finally tried the double verification thing and it seems to have worked so far . I just hope it lasts as I have read many accounts of users who had thought that the "SMTP server offline" problem was solved, only to have it resurface weeks or months later.

Thank you!

I started having this problem of not being able to connect to the gmail smtp to SEND mail from Apple Mail about 3 weeks after setting it up and having it work fine. I have SCOURED the internet looking for solutions. What has finally worked for me is alternating between enabling the 2-step verification and turning it off on my gmail account. First, it won't work, so I'll set up 2-step verification, enter the "special" password into my Mail preferences, then it will work. Later, it will not longer work, so I will disable the 2-step verification and then it will work. Go back to the beginning loop and start again.

Thank you for your help.

I have turned on two step verification and my iMac is now authorized.

However, I still can't send any mail from the mail aplication, getting the message:

Can not send message using the server smtp.gmail.com

My email account was rejected by the server - authentication required!

You mention to not forget to change the password in the SMTP server.

Maybe this is the problem?

How do I do that. Not the very long "don't have to remember" one I hope!

I also had this problem. I traced it down to using multiple email addresses for a single account. In my account settings I had configured my email address as "xxx@yyy.com, xxx@gmail.com", where xxx@yyy.com is my primary email. This allows me to select from which email a particular message is sent. It had worked well until recently, when I started getting the SMTP error messages. My troubles went away when I reversed the order of my email addresses - the gmail address must be in the first position. This didn't use to be a problem in the past, but apparently Apple's linking Mail's accounts to the Internet preference pane (which does not allow for multiple addresses on a single account) messed things up, and now only the first address is recognized for authentication purposes.

Could you explain this double email thing a bit better? I changed the spelling of my name and I set up a new email address that also uses the old one. This way, when people send an email to my old email address, it still gets to me. I think this might be the problem.

I'm going to also try the new Google help line. I sort of can't take it anymore. I'm thinking of ditiching google apps because of this. I set up so many of my organization & domain names through them.

This is just ridiculous. I've wasted two hours of my time trying to resolve this issue on a MacBook and to no avail. I've double-checked the settings with another MacBook where Apple Mail works fine with Gmail -- they were identical. On the problematic MacBook the incoming mail was synced OK but I was unable to send anything out. I've gone so far as deleting the user's e-mail account (it was a new account with next to nothing on it yet) and recreating it but it didn't help a tad. Finally we've settled on installing a different mail client and it worked like charm right from the start. Should've done that after the first 10 minutes wasted.

I've had the same issue, I resolved by going to Outgoing mail server (SMTP) setting in preference > Edit SMTP server list > password (that was blank initially). Insert the new password generated by google 2 step verification (i.e same as incoming server password).

have you configured the settings of your account correctly???

http://support.apple.com/kb/ht1277

Retype your password in the correct "Outgoing Mail Server" server