Windows 10: 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)

:)

 

Office 365 outlook will not send message to gmail accounts but receive

Let Outlook set your gmail account up. Port 25 is no longer used. These are the correct settings (leave SMTP at Port 587/TLS).
[table][tr]Incoming Mail (IMAP) Server imap.gmail.com Requires SSL: Yes Port: 993 [/tr] [tr][td]Outgoing Mail (SMTP) Server[/td] [td]smtp.gmail.com Requires SSL: Yes Requires TLS: Yes (if available) Requires Authentication: Yes Port for SSL: 465 Port for TLS/STARTTLS: 587[/td] [/tr] [/table]

 

Program cannot send email using smtp, gmail and port 587 and TLS

Hi Ariel,

Thanks for your reply. Windows Update says my main PC (A Lenovo Thinkpad Y50-70 running Windows 10) is up-to-date as of 4.11 PM today. I am running Acronis True Image 2015, build 6613, which Acronis says is up-to-date. I first noticed this problem 2 days
ago when I switched my email provider from sasktel to Gmail. Acronis had been using port 25 with no encryption to send email via sasktel for over a year, I switched it to use smtp.gmail.com using port 587 and TLS encryption (which is what Gmail recommends,
as they no longer support SSL on port 465). When I try to test a test message to port 587, Acronis gives me a Network Error within a second or two. When I try it using port 465, it gives me a Mail Server Error after about 20 seconds. My interpretation of that
is that when I specify port 587, the request doesn't even make it out of my home network. I have tried disabling my Norton Security firewall, and addeing a rule allowing 2-way traffic to smtp.gmail.com using any port. I have also tried disabling the firewall
on my NAT router. I'm wondering if for some reason requests to port 587 are not even getting past Windows.

 

Gmail in Outlook 2013 receiving not sending

Try using Outgoing port 465. It's working for me in Outlook 2013 (Gmail/IMAP)