Microsoft Outlook 2016 - Gmail not sending, asks for password for SMTP, tried different ports

[ReginaL]

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 3 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 tried ports 25 and 587 today, 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.

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

 

[Vince]

You can use either IMAP or POP3 to access your Gmail account . You can allow either or both in gmail.com Settings.

Here are my notes:

Office 2016 - To get the full options for email accounts (for easy editing)
File / Account Settings / Manage Profiles / Email Accounts / select one / Change

"Test Account Settings" should also work for each if configured properly.

------------

John Smith
john.smith@gmail.com
Account Type: POP3
pop3: pop.gmail.com
smtp: smtp.gmail.com

login: john.smith@gmail.com

Require login using Secure Password Auth. (SPA)

Outgoing server (SMTP) requires Auth
- Use same settings as my Incoming mail server

Ports (POP3): 995
- This server requires an encrypted connection (SSL/TLS)
Ports (SMTP): 587
- Use the following encrypted connection: STARTTLS

Delivery: (nothing selected)

----------------

Works for me. Not only that, but if you send an email to yourself in Outlook (through that gmail account) ... it shows in Inbox AND Sent Items ... in both Outlook and gmail.com . Pretty cool .

 

[ReginaL]

You can use either IMAP or POP3 to access your Gmail account . You can allow either or both in gmail.com Settings.

Here are my notes:

Office 2016 - To get the full options for email accounts (for easy editing)
File / Account Settings / Manage Profiles / Email Accounts / select one / Change

"Test Account Settings" should also work for each if configured properly.

------------

John Smith
john.smith@gmail.com
POP3
pop3: pop.gmail.com
smtp: smtp.gmail.com

login: john.smith@gmail.com

Require login using Secure Password Auth. (SPA)

Outgoing server (SMTP) requires Auth
- Use same settings as my Incoming mail server

Ports (POP3): 995
- This server requires an encrypted connection (SSL/TLS)
Ports (SMTP): 587
- Use the following encrypted connection: STARTTLS

Delivery: (nothing selected)

----------------

Works for me. Not only that, but if you send an email to yourself in Outlook (through that gmail account) ... it shows in Inbox AND Sent Items ... in both Outlook and gmail.com . Pretty cool .

Thank you. Unfortunately, neither 587 nor 465 is working for me now. 465 was working until about 3 days ago.

 

[Vince]

Did you find EVERY setting I mentioned? Remember, they are spread-out over 3-4 option-pages in Outlook-2016.

You might have to enable both POP3 and IMAP (Settings at gmail.com) for the troublesome account because I have them both turned on for my gmail account (I use it POP3 in Outlook, yet via IMAP on my iPhone/iPads).

What error are you getting?

Let me know. They are definitely correct because they work for me.

 

[ReginaL]

Did you find EVERY setting I mentioned? Remember, they are spread-out over 3-4 option-pages in Outlook-2016.

You might have to enable both POP3 and IMAP (Settings at gmail.com) for the troublesome account because I have them both turned on for my gmail account (I use it POP3 in Outlook, yet via IMAP on my iPhone/iPads).

What error are you getting?

Let me know. They are definitely correct because they work for me.

Yes I have tried those settings repeatedly over the last 3 days. They may work for you, but they do not work for me. If you do not to believe me, please do not waste any more of your time. Thank you.

 

[Vince]

Not really sure what you except to happen now. This doesn't even appear to be an Outlook problem. Maybe Gmail has a forum, but I think Google telephone based support is only for paid G-Suite customers. Someone else might drop into this thread, but I kinda doubt it. Plus, they would have to know something beyond what you and I already tried/posted. Pretty sure I can help you as we have the exact same config/services (using Outlook 2016 with free gmail as POP3). I have other relevant experience and credentials .

I understand your frustration, but after you calm down, I suggest you read my posts closer or even print them out. I think the answer is there, and if not, I can help you get it ... you just need to work the problem.

I still get the feeling you are not reading closely. I'm not much for repeating myself in forum posts.

Have you tried deleting the account from Outlook and re-creating it?

Do you understand that the online Settings at gmail.com I mentioned are separate for each Gmail account ?

Since you are using this account as POP3, have you tried proper settings in a different email client? Pretty sure Windows-10 has a free one called Mail. At least then you would know the settings are correct and you can move-onto some other piece of the puzzle.

 

[Vince]

< The "Enter your user name and password for the following server" message keeps popping up for the smtp.gmail.com server.

If this setting doesn't work:

Outgoing server (SMTP) requires Authentication
- Use same settings as my Incoming mail server

You can always try the other setting and re-enter your credentials. There is no magic there. It's just a time-saving feature when they are the same. It works either way.

 

[Vincenzo]

Hello Regina,
Google considers Outlook to be a "less secure app". You may need to enable a setting in your gmail.
Also if that still does not work, you can set up an "App Password".
Both are explained, somewhat, here:

Less secure apps & your Google Account - Google Account Help

Starting on September 30, 2024, less secure apps, third-party apps, or devices that have you sign in with only your username and password will no longer be supported for Google Workspace accounts.

support.google.com

 

[ReginaL]

Hello Regina,
Google considers Outlook to be a "less secure app". You may need to enable a setting in your gmail.
Also if that still does not work, you can set up an "App Password".
Both are explained, somewhat, here:

Less secure apps & your Google Account - Google Account Help

Starting on September 30, 2024, less secure apps, third-party apps, or devices that have you sign in with only your username and password will no longer be supported for Google Workspace accounts.

support.google.com

Hi Vincenzo, I have already double-checked to be sure "less secure apps" are enabled. I have checked 3 times in the last 2-3 days. Thank you for your time.

 

[ReginaL]

< The "Enter your user name and password for the following server" message keeps popping up for the smtp.gmail.com server.

If this setting doesn't work:

Outgoing server (SMTP) requires Authentication
- Use same settings as my Incoming mail server

You can always try the other setting and re-enter your credentials. There is no magic there. It's just a time-saving feature when they are the same. It works either way.

Thank you. Unfortunately, it does not work for me, and the message keeps popping up repeatedly. Thanks for trying though. Take care.

 

[ReginaL]

Not really sure what you except to happen now. This doesn't even appear to be an Outlook problem. Maybe Gmail has a forum, but I think Google telephone based support is only for paid G-Suite customers. Someone else might drop into this thread, but I kinda doubt it. Plus, they would have to know something beyond what you and I already tried/posted. Pretty sure I can help you as we have the exact same config/services (using Outlook 2016 with free gmail as POP3). I have other relevant experience and credentials .

I understand your frustration, but after you calm down, I suggest you read my posts closer or even print them out. I think the answer is there, and if not, I can help you get it ... you just need to work the problem.

I still get the feeling you are not reading closely. I'm not much for repeating myself in forum posts.

Have you tried deleting the account from Outlook and re-creating it?

Do you understand that the online Settings at gmail.com I mentioned are separate for each Gmail account ?

Since you are using this account as POP3, have you tried proper settings in a different email client? Pretty sure Windows-10 has a free one called Mail. At least then you would know the settings are correct and you can move-onto some other piece of the puzzle.

OK, thank you for your time.

 

[ReginaL]

Not really sure what you except to happen now. This doesn't even appear to be an Outlook problem. Maybe Gmail has a forum, but I think Google telephone based support is only for paid G-Suite customers. Someone else might drop into this thread, but I kinda doubt it. Plus, they would have to know something beyond what you and I already tried/posted. Pretty sure I can help you as we have the exact same config/services (using Outlook 2016 with free gmail as POP3). I have other relevant experience and credentials .

I understand your frustration, but after you calm down, I suggest you read my posts closer or even print them out. I think the answer is there, and if not, I can help you get it ... you just need to work the problem.

I still get the feeling you are not reading closely. I'm not much for repeating myself in forum posts.

Have you tried deleting the account from Outlook and re-creating it?

Do you understand that the online Settings at gmail.com I mentioned are separate for each Gmail account ?

Since you are using this account as POP3, have you tried proper settings in a different email client? Pretty sure Windows-10 has a free one called Mail. At least then you would know the settings are correct and you can move-onto some other piece of the puzzle.

OK, thank you for your time. I have read your posts, and I have completed those steps repeatedly over the past 3-4 days, after I read similar posts as well as instructions at official Google and Microsoft sites. I have successfully set up Gmail on Outlook on multiple laptops. Mine was working just fine until about 4 days ago. My repeating the same steps that I've already tried every day for 4 days is unlikely to change anything unless there is something going on with Gmail now, and that potential issue resolves. I am not questioning your "credentials" or the fact that your settings are working for you. Unfortunately for me, they are not working for me as of 4 days ago. Thanks and take care. Please do not waste any more of your time on this post. Doing so would not be a good use of your time, and your time is valuable.

 

[Vince]

Hello Regina,
Google considers Outlook to be a "less secure app". You may need to enable a setting in your gmail.
Also if that still does not work, you can set up an "App Password".
Both are explained, somewhat, here:

Less secure apps & your Google Account - Google Account Help

Starting on September 30, 2024, less secure apps, third-party apps, or devices that have you sign in with only your username and password will no longer be supported for Google Workspace accounts.

support.google.com

Thanks, that is helpful. I checked and Yes ... I have that ON as well. Here are my updated Outlook/Gmail notes that I keep (in case I ever have to re-setup gmail Account in Outlook):

Gmail Notes:
- You can use either IMAP or POP3 (in email client) to access your Gmail account . You can allow either or both in gmail.com Settings. I have both Enabled.
- If you send an email to yourself in Outlook (through the Outlook Account you have setup for Gmail) it shows in Inbox AND Sent Items, in both Outlook and Gmail.com (pretty cool).
- Since Outlook is considered "Less Secure" , in main Google Account Settings / Security (not gmail.com Settings) you must set "Less Secure App Access" to ON.
- It is working WITHOUT an App Password and I currently have 2-Step verification OFF.
- Less secure apps & your Google Account - Google Account Help

 

[ReginaL]

To be clear, in Google Security, "enable less secure apps" is ENABLED, and "two-step verification" is OFF. Thank you.

 

[ReginaL]

Thanks, that is helpful. I checked and Yes ... I have that ON as well. Here are my updated Outlook/Gmail notes that I keep (in case I ever have to re-setup gmail Account in Outlook):

Gmail Notes:
- You can use either IMAP or POP3 (in email client) to access your Gmail account . You can allow either or both in gmail.com Settings. I have both Enabled.
- If you send an email to yourself in Outlook (through the Outlook Account you have setup for Gmail) it shows in Inbox AND Sent Items, in both Outlook and Gmail.com (pretty cool).
- Since Outlook is considered "Less Secure" , in main Google Account Settings / Security (not gmail.com Settings) you must set "Less Secure App Access" to ON.
- It is working WITHOUT an App Password and I currently have 2-Step verification OFF.
- Less secure apps & your Google Account - Google Account Help

Settings are same here. Thank you.

 

[Vince]

To be clear, in Google Security, "enable less secure apps" is ENABLED, and "two-step verification" is OFF. Thank you.

It was a good fix-suggestion on his part.

And as far as "App Specific Passwords" I don't think they are required because:
a. Your existing credentials are working for POP3
b. I'm not using them (and mine works without one)

However, as a last resort, would be something to try. My iCloud email account requires them, but that is a different email service. They are kinda complicated to get setup and working so take it slow.

 

[ReginaL]

It was a good fix-suggestion on his part.

And as far as "App Specific Passwords" I don't think they are required because:
a. Your existing credentials are working for POP3
b. I'm not using them (and mine works without one)

However, as a last resort, would be something to try. My iCloud email account requires them, but that is a different email service. They are kinda complicated to get setup and working so take it slow.

Thank you. I will try it as a last resort.

 

[ReginaL]

It was a good fix-suggestion on his part.

And as far as "App Specific Passwords" I don't think they are required because:
a. Your existing credentials are working for POP3
b. I'm not using them (and mine works without one)

However, as a last resort, would be something to try. My iCloud email account requires them, but that is a different email service. They are kinda complicated to get setup and working so take it slow.

Vince,
I'm busy with Election Day volunteering but I just emailed Diane who runs this site to ask if I can book time with her later this week. If you feel like you can solve this issue, please feel free to message me your rate, as I believe I will have to deal with this more post-Election. I also created a "test" gmail account and tried to add it as a POP account into Windows Mail - I could not send or receive emails. When I added that same gmail account to Windows Mail as an IMAP account, I was able to send a receive emails.

 

[Vince]

Vince,
I'm busy with Election Day volunteering but I just emailed Diane who runs this site to ask if I can book time with her later this week. If you feel like you can solve this issue, please feel free to message me your rate, as I believe I will have to deal with this more post-Election. I also created a "test" gmail account and tried to add it as a POP account into Windows Mail - I could not send or receive emails. When I added that same gmail account to Windows Mail as an IMAP account, I was able to send a receive emails.

I appreciate your confidence in my skills (and sure we could fire-up the AnyDesk), but this is Diane's site, let's let her help you.

I figured you would try your broken account in Windows Mail, but I suppose a new test account is the same idea.

Interesting results. If POP is allowed in Gmail.com Settings, I wonder why it is not working. Was it still complaining about the password or a different error this time? Not sure if your ISP or local Firewall blocking ports would cause something like that.

 

[ReginaL]

I appreciate your confidence in my skills (and sure we could fire-up the AnyDesk), but this is Diane's site, let's let her help you.

I figured you would try your broken account in Windows Mail, but I suppose a new test account is the same idea.

Interesting results. If POP is allowed in Gmail.com Settings, I wonder why it is not working. Was it still complaining about the password or a different error this time? Not sure if your ISP or local Firewall blocking ports would cause something like that.

Hi Vince,
This was my first time trying Windows Mail. With Windows Mail configured as POP, the email I tried to send just sat in the Outbox, and no error message was generated to my knowledge. I don't have enough experience with Windows Mail to know if an error message typically pops up.

With emails I was to receive, the Windows Mail inbox simply sat empty (but when it was configured for IMAP, I received emails). No errors popped up though. I'd describe it as "nothing appearing to happen." I waited several minutes, as well as deleting and re-adding the POP "tester gmail" to Windows Mail 3 times. Whereas, with IMAP, Windows Mail was functioning immediately. I don't even know what an error message looks like in Windows Mail. Anyway, I'm leaving Los Angeles tonight for 2 days of out-of-state election volunteering, so I hope to be able to find a solution when I'm back Wed/Thurs.

Since you thought this might not be an Outlook problem, I also posted in a Windows Ten forum, Google forum, and in Microsoft Community.

As you said, perhaps Charter Spectrum cable or Avira is blocking ports. I do not know.

Thank you. I really do appreciate your trying to help. I honestly had already tried the advice you offered - multiple times over these past 3 days, as I have encountered very similar issues in the past and either somehow managed to "fix" them or they just appeared to go away on their own. Once I hired a local tech support guy (whom I'd used before at work), he went through about an hour of troubleshooting, the error didn't go away, and then a couple days later, the "Enter your user name and password" stopped popping up on its own. I guess maybe Google had some issue at that point as I had the error when my Outlook was on my home wifi as well as when it was on the office network. But at that point, the pop up was merely annoying and I was still able to send and receive email. This is the first time I haven't been able to send email. But if that's my biggest problem in life, then I should count my blessings! Though I still want/need to get rid of the problem!