My Mail in Yosemite doesn't work!

I am having problem with my Mail in Yosemite OS, hotmail is fine, only gmail has problem. I can receive emails, but i can send mails with gmail. Every time I try to send an email with my gmail in Mail, it tells that "Cannot send message using the server smtp.gmail.com:(my gmail user name)." it also says "The gmail SMTP connection to server smtp.gmail.com failed."


What should I do? I need to send tons of emails each day, and now i have to write my emails on my iMac, then open it in my iPhone 6 to send emails!

iMac, OS X Yosemite (10.10)

Posted on Oct 20, 2014 7:39 PM

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31 replies

Oct 21, 2014 11:31 AM in response to Erik.W

Erik, I was having the same problem. this is what I did and it appeared to take care of it. I must have had an old password in my "send mail server" that was causing my issue. BTW, I was getting the same error that you mentioned.


1. Open mail and then Open Preferences -> Accounts Information

2. Click on dropdown next to Outgoing Mail Server (SMTP) and click "Edit SMTP Server List"

3. Click on "Advanced"

3. Change "User Name" to "b...@customdomain.com" and re-enter your password (Password was my problem)

4. Click OK.

The dropdown should no longer say (Offline)

Oct 23, 2014 8:07 AM in response to Erik.W

I had the same problem, but I fixed it quite easily. In my case it was due too the 2-step-verifaction that I activated for Gmail. Shortly explained, you need to generate a (new) password just for the Mail App on your Mac. So, please try these steps:


1. Go to this page: https://support.google.com/accounts/answer/185833?hl=en

2. Click on the link 'App passwords'.

3. Login if required.

4. Now you will see a list with devices and applications that have a special Google password. If you see a password for the Mail App, delete it and create a new one.

5. Now put this new password in your settings of your Mail App.


This should do the trick.

Oct 24, 2014 9:46 AM in response to Mac-Freak

I'm having a similar issue to Erik, my Apple's native mail app works fine when I am use my home wifi but refuses to connect via internet connections at coffee shops et cetera.


At the coffee shops, the wifi connects, I can browse the internet, but my mail boxes will not update. The "connection doctor" displays the infamous red dot. The error listed for Gmail cites an inability to connect to both the SMTP server and the IMAP server. iCloud also is unable to connect via IMAP server.


I've tried toggling SSL within the advanced connection options but get the same result.


The only difference between using the Coffee shop wifi and my home wifi is once I connect to the internet at the coffee shop, I have to click a "terms of use" verification box... I wonder if that could be interfering with my mail connection? If so, are there any ways to remedy the issue?


Thanks for the help/ideas!

Oct 25, 2014 6:14 AM in response to Mac-Freak

Also don't forget, if you do have a 2-step-verification for your Gmail account, be sure to ALSO change the password in the Outgoing Mail Server settings as well. This was my problem.


1. After receiving the new app password from Google, Open Mail

2. Click on Mail and Go to Preferences

3. Highlight your Gmail account

4. Find the "Outgoing Mail Server (SMTP) section and click the drop down menu next to it.

5. Click the Drop Down menu and click "Edit SMTP Server List..."

6. Highlight the Gmail account at the top

7. Click the "Advanced" Tab below

8. Verify the User Name is Correct (I recommend putting username@gmail.com)

9. Enter the new generated password you received from google into the Password box.


This explained why I was Receiving my Gmail messages but I could not Send my messages. So be sure to put the password in both the "Incoming Mail Server" section and the "Outgoing Mail Server" section.


Hope this helps some of you.

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My Mail in Yosemite doesn't work!

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