Intermittent Failure to Send OUTLOOK.COM Emails Within Outlook 365 On My PC

Topic

New Reply

Periodically, when I send an email using Outlook 365 on my PC, the message will not be sent and I’ll be prompted for my email address and password repeatedly.  Typically speaking if I exit Outlook 365 and return later on the message will go through.  I put a post out on Microsoft’s Community Forum and someone sent me  a link to an article entitled “Modern Authentication Methods Now Needed To Continue Syncing Outlook Email from Non-Microsoft Email Apps”

In this article it stated that if I was using an email client like Thunderbird I would soon need to change it to use Oauth2 instead of a password and that right now there would be intermittent failures to send messages that would result in repeated password prompts.

Well, I’m confused as the article was in reference to non-Microsoft Email Apps but it also appears to reference older versions of Outlook.  But at the same time, I’m seeing the repeated intermittent failures to send in my copy of Outlook 365 that’s part of my current subscription to Microsoft 365.

I tried to create a new account for my outlook.com email address and when  I did, the only option I had was to provide my password with no option to setup OAuth2 within Outlook 365.  So, has anyone else been seeing intermittent email send issue from Outlook 365 and know what the problem is assuming that it’s unrelated to the requirement for other email clients to use OAuth2 instead of a password?

Reply | Quote

Replies

Create a new profile (and add account) as indicated in that article:

If you use Outlook for Windows:

Outlook supports Modern Authentication in all current Microsoft 365 subscription SKUs and Outlook 2021 LTSC (any SKU with build 11601.10000 or higher) when connecting directly as Outlook.com. If your Outlook is configured to connect to Outlook.com using POP or IMAP, Modern Authentication is not supported. This means that when Basic Authentication is fully deprecated, it will no longer connect. For this scenario, you have a few options:

[Option 1: Not applicable to Microsoft 365]

Option 2: Switch to Outlook.com/Exchange Syncing

Instead of using POP/IMAP and SMTP, create a new Outlook Desktop profile and then add your Outlook.com account using automatic account configuration, which will add the account with Modern Authentication. To do this, please use the following guidance:

Create a new Outlook Desktop profile. For more information, please go to Create an Outlook profile.

Add your Outlook.com account. For more information, please go to Add an email account to Outlook.

Modern Authentication Methods now needed to continue syncing Outlook Email in non-Microsoft [sic] email apps

Reply | Quote

B,

I’m still a bit confused.  When you asked if I was using Outlook for Windows did you mean the Email client that part of Office 365 or were you referring to other email apps that Microsoft called Outlook?

If you’re referring to the Outlook email client that’s part of Office 365 then I might have a larger problem.  The way I have Outlook 365 setup is that I actually have my POP3 settings configured for one email address and my outbound server configured for my outlook.com email account.  I automatically forward all of my outlook.com emails to an alternate email account so my emails are double scanned for spam (I get a lot of spam) but I have my SMTP server setting configured to use outlook’s SMTP server so if anyone’s examining the email headers they cannot discover my alternate email address as I never send or receive any email using that email address.  If you’re saying that OUTLOOK 365 is part of this modern authentication method switch and the only option is to use a password in the SMTP settings then is OUTLOOK 365 being thrown in the trash heap?

Your second option was to setup Exchange Syncing but given the 2 different servers I use for inbound and outbound email, is there a way to setup my current configuration using Exchange Syncing?

Reply | Quote

Moondoggy wrote:

I’m still a bit confused. When you asked if I was using Outlook for Windows did you mean the Email client that part of Office 365 or were you referring to other email apps that Microsoft called Outlook?

I didn’t ask; I was just quoting the article. But “If you use Outlook for Windows:” refers to any Outlook on Windows.

I left out Option 1 as it only said that Outlook 2007, Outlook 2010, Outlook 2013, Outlook 2016 MSI, Outlook 2019 LTSC would no longer work for Outlook.com; so that didn’t apply to you.

Moondoggy wrote:

If you’re referring to the Outlook email client that’s part of Office 365 then I might have a larger problem. The way I have Outlook 365 setup is that I actually have my POP3 settings configured for one email address and my outbound server configured for my outlook.com email account. I automatically forward all of my outlook.com emails to an alternate email account so my emails are double scanned for spam (I get a lot of spam) but I have my SMTP server setting configured to use outlook’s SMTP server so if anyone’s examining the email headers they cannot discover my alternate email address as I never send or receive any email using that email address. If you’re saying that OUTLOOK 365 is part of this modern authentication method switch and the only option is to use a password in the SMTP settings then is OUTLOOK 365 being thrown in the trash heap?

That sounds complicated, but it might still work as the change only affects Outlook to/from Outlook.com. I don’t really understand your last sentence but Outlook 365 is certainly not being thrown in the trash heap.

Moondoggy wrote:

Your second option was to setup Exchange Syncing but given the 2 different servers I use for inbound and outbound email, is there a way to setup my current configuration using Exchange Syncing?

It’s the only option for Outlook.com, but I don’t see why messages forwarded from there would not still arrive in the other account.

(I think the article was composed by an incompetent team, as you can tell by “non-Microsoft” in the headline when nearly half the page is about Outlook.)

Reply | Quote