I found alot of people having your same issue.
The trick seems to make sure you entered the NEW password ***** all the right places.
14 down vote
The application-password ***** you create will need to be added in two places in your Apple Mail app.
There is your Incoming Mail Server password, which is immediately visible under your account information.
Below that you can see the selection for Outgoing Mail Server (SMTP). The default will be Gmail. Click on the drop down box and select "Edit Server List".
Here you will discover that you actually need to enter that application-password ***** second time. Put it in here and you're done.
Check the issue with the last suggestion and you should be good to go. If not please let me know.
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 ***** 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 ***** 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 ***** my APPLE MAIL and used that new password ***** my APPLE MAIL gmail password. Don't forget to change the password ***** the SMTP server as well.
I used the same password ***** 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!
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How to resolve Mail SMTP errors in OS X 10.10.4 and iOS 8.4
By AppleInsider Staff Thursday, July 09, 2015, 11:37 pm PT (02:37 am ET)
A change in the way OS X 10.10.4 and iOS 8.4 handles security keys has caused a number of users — specifically those using Gmail — to see SMTP send failures and even app crashes. Luckily, there's an easy fix for both users and system admins looking for a permanent server-side solution.
The issue was first noted by users on Apple's Support Communities forum shortly after Apple released OS X 10.10.4 and iOS 8.4 on June 30. Sporadic account connection issues, inability to send email from specific servers and complete Mail shutdowns were reported.Apple offered a possible explanation in a support document one day later, saying that both OS X 10.10.4 and iOS 8.4 provide increased security against a certain TLS vulnerability called "Logjam." To protect users, devices updated to the latest OS versions no longer connect to servers or webpages using "weaker" Diffie-Hellman encryption, defined as having a group size of less than 2,048 bits.As a result of the poorly documented change, users might encounter problems when connecting to enterprise class Wi-Fi (802.1X), secure email connections (SMTP), secure web connections (HTTPS) and secure Internet printing (IPP over TLS/SSL), Apple said.Support Communities forum members have discovered a number of workarounds, including the disablement of SSL, which is not recommended considering it removes a layer of protection.
A more viable fix can be accessed by navigating to Preferences option in the Mail for OS X menu dropdown. In the Settings window, click on the Accounts icon and select the email account experiencing issues.
Next, click on Advanced in the resulting pane, toggle the check box next to the "Automatically detect and maintain account settings" item line and restart Mail. Upon opening, navigate back to the affected account and tick the box if you turned it off, or confirm that it remained checked upon restart.