Outlook Email Connection Error

I have a Gmail account that normally works flawlessly with my Outlook 360 account.  All of a sudden I started getting the attached error message whenever I try to send an email.  I went into Outlook Account Settings to confirm that the password hadn't been changed or corrupted, and when I hit "OK" the email goes through just fine.  So my settings seem OK.  What is causing this and what can I do to fix it?

Outlook email error message
Thanks,

Phil
philsimmonsAsked:
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John HurstConnect With a Mentor Business Consultant (Owner)Commented:
Check the ports you are using under Advanced Account settings. You probably need 995/SSL for incoming mail and 465 or 587/SSL or TLS for outgoing mail.

Make sure under Outgoing Server that you have authenticated properly. This affects sending and that is where you have an issue.

Looking at the picture, did you select (check) Save Password.

I had a similar issue with my mail.com account. All settings were correct and worked. But the error popped up and I could OK it. I had to install a certificate. The need for the certificate popped up when I clicked OK.
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suriyaehnopConnect With a Mentor Commented:
Your Outlook Account settings configured based on Outlook 365? Based the screenshot, it seem that you used Outlook to configure IMAP/POP to sync your GMAIL account. Make sure your IMAP/POP for GMAIL is configured correctly.
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philsimmonsAuthor Commented:
Thank you!
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John HurstBusiness Consultant (Owner)Commented:
Phil - Thank you and I was happy to help.
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