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The server for account "Gmail" returned the error "[ALERT] Too many simultaneous connections. (Failure)." Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

Continually receive this message when working - can not be on Safari and doing email at same time. I talked to Apple support and they say it is a Microsoft issue and Microsoft says it is an Apple issue, but very very painful to keep getting this message all day.


Thanks

iMac, Mac OS X (10.7.4)

Posted on Aug 16, 2012 12:01 PM

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10 replies

Feb 12, 2016 8:16 PM in response to wakelycharles

I see that this is an old post, but after fighting with Outlook for over a year to get my mail, I FINALLY got it working again.


The first thing I had to do was log into my my Gmail account and turn off the button labeled "Less secure apps" as Outlook is in that category.

  1. Go to the "Less secure apps" section in My Account.
  2. Next to "Access for less secure apps," select Turn on. (Note to Google Apps users: This setting is hidden if your administrator has locked less secure app account access.)

And if you have 2-step verification on (as I did), it will still make Outlook fail. So the next thing you have to do is create an app password which will generate a password for you, and you use that in Outlook for it to sync correctly.


  1. Visit your App password page. You may be asked to sign in to your Google Account.
  2. At the bottom, click Select app and choose the app you’re using.
  3. Click Select device and choose the device you’re using.
  4. Since Outlook will not be listed, select Other and type in Outlook for future reference.
  5. Select Generate.
  6. Follow the instructions to enter the App password (the 16 character code in the yellow bar) on your device.
  7. Select Done.
  8. Copy the password that was generated.
  9. Open Outlook and paste the password in the Password section. DO NOT use your regular password.
  10. Your mail will sync without anymore issues. (Hopefully)

Once you are finished, you won’t see that App password code again. However, you will see a list of apps and devices you’ve created App passwords for.

I hope this helps everyone who is having an issue. And I hope these directions are easy to follow! Good luck everyone! :-)

The server for account "Gmail" returned the error "[ALERT] Too many simultaneous connections. (Failure)." Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

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