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I have a user running still running on Windows XP + Outlook 2007. He uses a google apps email account through IMAP w/ SSL on port 993

Recently he's started receiving an error message shown here. Error Message Certificate Error message

The time on this computer is properly set and all updates have been installed (include the optional root certification updates)

https website work without a problem it's really only outlook that is seeing this error. Doing a lot of searching on google before posting I also came across some people saying to clear the SSL state in Internet Explorer under Internet Options -> Content -> Clear SSL state and I've also reset the internet Explorer settings as well.

Would anyone here suggest any additional troubleshooting to try to get this error "silenced" at the very least?

  • The date on the certificate, is that to 4th August 2014, or to 8th April 2014? – Kinnectus May 29 '14 at 13:44
  • @BigChris that's August 4th – Nick M. May 29 '14 at 13:46
  • Is the outgoing mail server address correct? instead of "imap.example.com" should it be "smtp.example.com"? – Kinnectus May 29 '14 at 13:46
  • @BigChris I believe we are getting the cert error on the incoming imap.gmail.com and not the outgoing – Nick M. May 29 '14 at 13:49
  • And you've gone through the GMail's official instructions to adding an IMAP account to Outlook? (have to ask to rule out something stupid!) – Kinnectus May 29 '14 at 13:52
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Open Outlook > Click ‘Tools’ from the top menu > Select ‘account settings’ from the ‘tools’ menu > Highlight the email account you are having trouble with and press ‘Change’ > From the ‘Change e-mail account’ page click on ‘More settings’ >From the ‘Internet email settings’ page choose the ‘advanced’ tab >Un-tick the ‘This server requires authentication’ option > click ‘OK’, then ‘next’ then ‘Finish’

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After many hours of troubleshooting this issue I ended up upgrading this user to the latest version of office (2013). This appear to have fixed the certificate error they were receiving.

Hope this ends up helping someone else in the future and saving them endless hours troubleshooting!

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