Alford7

Q: Can't send email from iMac

Screen Shot 2015-10-15 at 10.51.16 AM.png

 

All of a sudden, I couldn't send email from Mail with my iMac (2013 late) from my Google account.  The above message appeared.  So I deleted the email account from Mail and then added the same account back in the hope that it fixed itself ... it didn't.  The above message still appears and it is not allowing me to add a new email account.

 

I wonder if anyone can help fixing this problem.  Thank you in advance.

 

Alford

iMac, OS X El Capitan (10.11)

Posted on Oct 15, 2015 10:04 AM

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Q: Can't send email from iMac

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  • by Eric Root,Solvedanswer

    Eric Root Eric Root Oct 17, 2015 11:42 AM in response to Alford7
    Level 9 (71,160 points)
    iTunes
    Oct 17, 2015 11:42 AM in response to Alford7

    Try going to Applications/Utilities/Keychain Access and deleting the Google server certificate.

  • by Alford7,

    Alford7 Alford7 Oct 17, 2015 11:42 AM in response to Eric Root
    Level 1 (1 points)
    Oct 17, 2015 11:42 AM in response to Eric Root

    Thanks Eric.  I deleted all those invalid certificates and finally got Apple Mail to add the Gmail account for me.  Unfortunately, it was not straight forward for me and it took me two rounds of investigation before it worked so I will write in detail how my problem was solved so people don't have to spend as much time as I did.

  • by Eric Root,

    Eric Root Eric Root Oct 17, 2015 11:47 AM in response to Alford7
    Level 9 (71,160 points)
    iTunes
    Oct 17, 2015 11:47 AM in response to Alford7

    You are welcome.

  • by Alford7,

    Alford7 Alford7 Oct 17, 2015 12:05 PM in response to Alford7
    Level 1 (1 points)
    Oct 17, 2015 12:05 PM in response to Alford7

    My problem started after updating OS to El Capitan.  Mail app on my iMac could not connect to my Gmail account with the following prompt / error screen: "Connection Insecure.  Failed to verify the server certificate.  This could be because of your network configuration or your proxy settings."

     

    Screen Shot 2015-10-15 at 10.51.16 AM.png

     

    I went to the Keychain Access screen by way of:

     

    1. Click Finder icon

    2. In the window that comes out, click Applications located in the left pane of window.

    3. Then click the Utilities folder

    4. Click Keychain Access (you should then see the following screen)

     

    Screen Shot 2015-10-17 at 11.49.05 AM.png

    5. You will see that on the left of screen under Keychains, select "login".  Then under Category, select "My Certificates".

    6. Once "My Certificate" is selected, you go thru each shown in the main screen to see if there are messages in red with a "X".  As shown in the above printscreen, I had one showing "This certifcate has been revoked".  When you find any certificates with error, delete them.

    7. Then select "Certificates" under the Category section on the left lower pane of the window.  You will see the below window.  Also go thru each certificate in the main screen, delete all with an error.

     

    Screen Shot 2015-10-17 at 12.31.02 PM.png

     

    8. When done, restart Mail app by clicking Mail/Quit Mail in the menu while Mail app is opened.

    9. Add your Gmail account by clicking Mail/Add Account shown below.

     

    Screen Shot 2015-10-17 at 12.33.51 PM.png

     

    I finally got it working.  Thanks Eric Root!

  • by Eric Root,

    Eric Root Eric Root Oct 18, 2015 8:20 AM in response to Alford7
    Level 9 (71,160 points)
    iTunes
    Oct 18, 2015 8:20 AM in response to Alford7

    You are welcome.

  • by raschica,

    raschica raschica Nov 9, 2015 7:12 AM in response to Alford7
    Level 1 (0 points)
    Nov 9, 2015 7:12 AM in response to Alford7

    I was having the same problems. I followed your instructions and it worked. Just wanted to say thanks.

  • by raschica,

    raschica raschica Nov 9, 2015 7:24 AM in response to Eric Root
    Level 1 (0 points)
    Nov 9, 2015 7:24 AM in response to Eric Root

    I was having the same problems. I followed your instructions and it worked. Just wanted to say thanks.

  • by Eric Root,

    Eric Root Eric Root Nov 9, 2015 8:21 AM in response to raschica
    Level 9 (71,160 points)
    iTunes
    Nov 9, 2015 8:21 AM in response to raschica

    You are welcome.

  • by sfraser,

    sfraser sfraser Nov 15, 2015 9:11 AM in response to Alford7
    Level 1 (0 points)
    iOS Apps
    Nov 15, 2015 9:11 AM in response to Alford7

    I was having the same problem - after upgrading to El Capitan, on some OS X machines accessing Google email from Mail stopped working. You would get the certificate error reported by others on this thread. I found three expired certificates in the keystore and deleted them - didn't help. I then went through the keystore and deleted all google related items - still didn't help. (All the while rebooting between these changes just to be sure the keychain items weren't cached).

     

    Next I tried deleting the Internet Account for Google Mail and re-adding - and got the same certificate error!

     

    It occurred to me I was on an account with Parental Controls enabled. So I logged in to a different account that did not have Parental Controls, and did not have a Google Mail account set up. It worked fine!

     

    So then I disabled Parental Controls for the problem account, went back to it - and things worked.


    (To be clear what I mean is click "Allow unrestricted access to websites" in Parental Controls for the problematic account.)

     

    It appears to me that there is a defect in El Capitan related to parental controls and how Google Mail accounts are set up. I would guess that when the dialog pops up and asks you to Sign In to Google it is proxied through OS X's Parental Controls and unless you have some specific hostname allowed, it fails. Normally OS X pops up a dialog and asks you if you want to allow a site - in this case that never happens, and you get the Certificate Error - probably because Mail get's a blank response back from the parental controls proxy.

     

    So for people having the issue on this thread - if you are also using Parental Control, try disable them entirely for the account in question and that may fix things for you.