Windows 10: Outlook365 is no longer sending emails, error 0x800CCC1A and SMTP box repeatedly pops up...

I'm using Windows 10, I did a Windows Update on 13/01/2021 and the emails sent okay on 14/01/2021 but since then have been unable to send mails from Outlook, for my POP3 personal gmail address, so I'm unsure if its related to the latest update or not. I don't like IMAP so please don't suggest I change to IMAP. The other work related email still sends fine, downloaded into the same Outlook account but separate inbox etc. I made no changes to my outlook settings and its all been working fine till now. Emails still receiving normally. I've tried a number of fixes, including changing SMTP settings from 465 to 597 but Outlook will not allow any repairs or changes, it says "failed". Please help, I have set up my Outlook account with many folders and i have no wish to change to the gmail browser for my emails, or to another system if I don't have to; I would really like to simply fix this problem so that my emails send again, thank you! CharlotteD

:)

 

Changing internet standards for emailing from SMTP to POP

Smtp is the sending/outgoing server while pop is used for incoming.

Which email client & email account are you using?

Who or what is informing you to change smtp to pop?

 

Best Practices for Outlook365 and WP8.1

Suppose the following:

• You walk into a Microsoft Store.
• You pay $99.99 for Office365.
• You pay $399 or more for a WP8.1.
• You pay $599 for a new laptop with Windows 8.1.
• You go home.
• You have Outlook 2007 and you have backed it up to a PST file, email, contacts and calendar.
• You successfully install and active Office365 onto your new Windows 8.1 laptop.

Here is your situation:

• Your new Windows 8.1 laptop with your new Office365 is a blank canvas.
• Outlook365 has nothing in it. In fact, you have not even opened up Outlook365 for it to guide you through its first use.
• Your new WP8.1 is just sitting there. It has not been turned one yet for it to guide you through its first use.

Here is your goal:

• You want Outlook365 to sync with you WP8.1.
• You want your email to show up on both Outlook365 on your Windows 8.1 laptop and on your WP8.1. You want to send and to receive email from either device.
• You want your calendar to show up on both Outlook365 on your Windows 8.1 laptop and on your WP8.1. You want to manage your calendar from either device.
• You want your contacts to show up on both Outlook365 and on your Windows 8.1 laptop and on your WP8.1. You want to manage your contacts from either device.

What is the step-by-step procedure a Microsoft customer must take so that the customer achieves the above goals such that:

• All of the above goals work 100%.
• There are no errors.
• There are no duplicates.
• There are no omissions.
• There is 100% confidence in the $1,098.99 worth of Microsoft products that you got what you paid for.
• There are no excuses for why it is OK Fine and Hunky Dory that you spent $1,098.99 and it does not work.
• There is no blaming a 3rd party that it may be the culprit of the problems.
• The Microsoft customer enjoys using the $1,098.99 of Microsoft products rather than having a daily battle to try to get it to work.
• The $1,098.99 of Microsoft products work as well as the free Google stuff.
• The Microsoft customer does not regret making a decision that has gone horribly wrong.

Anyone got any ideas?

 

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)