Outlook 2016-Gmail not sending, password for SMTP, tried ports 465 587

Hello,

Thanks in advance for your time. I have 2 Gmails set up in Outlook 2016. My back-up Gmail is set up as an IMAP/SMTP account, and it's working fine (no jinx). My primary email is set up as POP/SMTP, and as of approximately 4 days ago, I can no longer send email from Outlook. The "Enter your user name and password for the following server" message keeps popping up for the smtp.gmail.com server. (In the past, when I've received this pop up, I've spent hours troubleshooting, and then 1 or 2 days later, the pop ups eventually cease on their own. I've assumed something was going on with Google, they resolved it, and my problem ceases.)

This time, I've tried port changes, and I can see on support forums that other people have had similar problems over the last few months. For the past several years, Outlook SMTP has been set to port 465 (SSL/TLS) with no problems. I have tried ports 25 and 587, but no luck.

I am able to receive email when I restart my Outlook. Upon restart, the "Enter your user name and password for the following server" message pops up once for the pop.gmail.com server, and when I hit "OK," Outlook accepts my password, and the error ceases. However, Outlook will NOT accept my password for the SMTP server.

In Google Security, "enable less secure apps" is ENABLED, and "two-step verification" is OFF.

Please let me know if you have tips. Thank you so much. My OS - Windows 10 Pro, Version 1909 (OS Build 18363.1082)

Try3 said:

The port 465 matches what GMail says. Have you checked all your other settings against the GMail recommendations?

Check Gmail through other email platforms - GoogleSupport

Denis

Yes, I have checked and tried re-setting multiple times. Thank you.

Try3 said:

I'm an idiot. I misread your original post. The problem account is pop. I posted the wrong link before.

SMTP 465 settings do not match what GMail says for a pop account but I can see that you have tried 587 as well. I have not got around to changing mine yet and my SMTP is still 465 yet it works.

Read Gmail messages on other email clients using POP - GoogleSupport
The troubleshooting section might also have some useful content.

You don't say when the problem started. Any change to Office / Windows / your ISP?

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These are my GMail pop settings in Outlook 2007 [and they have not been changed since 13th April 2015 if not longer]. I used them to send an email yesterday without any problems.

Outlook, GMail 1 Main dialog [Office 2007]


Outlook, GMail 2.1 More settings, General


Outlook, GMail 2.2 More settings, Outgoing server


Outlook, GMail 2.3 More settings, Connection


Outlook, GMail 2.4 More settings, Advanced

Outlook 2007 does not have TLS/StartTLS so I use SSL



Denis

Thank you, Denis. The SMTP setting is no longer working for me. I have not had a problem in a few years, but it stopped working for me within the week. I had mine set the same way. I've been experimenting with 587 but that's not working for me either.

Thank you all so much for your time. The problem was having to unlock Gmail Captcha. I do not think I received a warning from Google to unlock Captcha, but that's what it took. Thanks again!!