Settings for using Outlook/Hotmail SMTP via Gmail

Yes, I’ve tried those settings. I just tried it again. It failed, giving the message “Authentication failed.” I get that whether I use the full e-mail address or merely the e-mail user name absent the @outlook.com — see the window below, and that was the second try, without @outlook.com.

On the page where it starts, for Name, I am using the actual user name of the overall Hotmail account, which is different from the moniker used for the e-mail address. In the past, I have tired using the actual moniker of the e-mail address, it made no difference. 

In the settings popup, I am not offered STARTTLS, only TLS. I am not offered Authentication Method at all. 

Baffling.

The pop ups in gmail, below:

That will not work after mid-Sept (and will be flaky until then) - unless Gmail changes it to support modern authentication. Right now, it is basic auth only.

And your SMTP server settings are wrong....

From:

POP, IMAP, and SMTP settings for Outlook.com - Microsoft Support

Well, I’m pushing in the emails that come into Hotmail/Outlook from Hotmail to Gmail. I do that from Settings/Mail/Forward and IMAP. They are all going to Gmail just fine, even those coming into my Outlook aliases in Hotmail. 

It is when I then send from Gmail under the name of one of those aliases (they come into gmail as from the alias, so clicking the Reply button sets them up to respond to the sender via the same alias address. I believe I can initiate a new e-mail via an Outlook alias too, although I don’t generally do that.) 

We have been talking about the settings in Outlook for that.

I do also have both POP and IMAP set up in Gmail. That is under Settings/Forwarding and POP/IMAP. My configuration has been unchanged for many years now. It is only earlier this year that this problem started. 

But first, what we are talking about is under the Accounts and Import tab instead. The Forwarding and POP/IMAP tab seems to be merely for forwarding my Gmail e-mail. I believe I did that when I had some issue about e-mail in Gmail that was not in Outlook. It id not sending all my Gmail to Outlook.

Under Accounts and Import, under Snd mail as:, I do have the Outlook aliases listed there. That is where I have been trying to get the settings right all through this discussion.

The default setup there is to send as my main Hotmail address. That works fine. It’s those Outlook aliases that do not work anymore, they used to. The one I have been using in recent times is sent with :

Mail is sent through: smtp.office365.com

Secured connection on port 587 using TLS

And I have explained the issue with even trying to change the SMTP setting.

On another, which I have not used in a long time, it is set as:

Mail is sent through: smtp.live.com

Secured connectin on port 25 using TLS.

And for another, it is sent through SMTP Server: 

hotmail-com.olc.protection.outlook.com

Secured connection is on port 587 using TLS

And for all, I have checked:

Reply from the same address the message was sent to

All of those were set up as they were supposed to be when set up. It appears Hotmail/Outlook has been constantly changing the settings to use, who can keep up with it so many times! I haven’t used any of those others, only the one alias in recent times. One of the others, I see, it’s even called Testing, l guess for when I was testing things. 

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I was not using Outlook as the interface for gmail, I was doing it the other way around, using Gmail as the interface for Outlook. That still works for my primary hotmail account. It's the Outlook alias names for that account that are now the problem when using Gmail as their interface and trying to send e-mails under the Outlook alias, that's what stopped working, the sends are being rejected.

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Yes, that is not a connected account.

Do you have the aliases set up in Gmail as available for sending?

Do you have the account added to gmail.com as POP account? That will stop working next month.

Thank you. Diane. I did follow your lnk to your Website. Very good info. (I recommend any other readers also check that out, she has a large wealth of information there about all things Outlook. She's a top Outlook expert.)

I'm now a bit confused about what I was doing and whether it was "connected accounts" or not. For one thing, I was not using Outlook as the interface for gmail, I was doing it the other way around, using Gmail as the interface for Outlook. That still works for my primary hotmail account. It's the Outlook alias names for that account that are now the problem when using Gmail as their interface and trying to send e-mails under the Outlook alias, that's what stopped working, the sends are being rejected. I have been doing that with I think all my Outlook aliases for the Hotmail account since before 2021. (Read at her link, that toime frame is significant.)

I don't know if how I was doing things is part of this "connected accounts" thing. I have all of my Hotmall account forwarded to my Gamil account as it comes in. And I deal with it there. I make those Outlook aliases in Hotmail. In gmail, I link the aliases to Hotmail/Outlook and send. They send as the alias Outlook account via the already established link.

Now I see they are not sending, I gather Hotmail/Outlook is rejecting them. If this is a security issue, hey, I have them officially linked from Gmail to Hotmail, I specifically set that up. It reminds me of setting up an ACH transcation from one bank to another. When I set that up,a nd espeiclaly when I have used it for yeafrs, I dont see how that is any security issue, or an automatic deposit. I, the Hotmail account owner, have never complained or even alaerted Hotmail to any problem. They can simply send me an alert that such has been set up (and they might actually do that, its a long time since I set things up, I don't recall if they do).

(I note, I'm not doing anything nefarious with them. I'm not spamiming with them, or scamming, or anything else. They are for various reasons, from just not wanting to use my main Hotmail account in order to avoid possible spam, maybe from some palce I signed up with for something, but don't want their spam, to simple privacy for certain things. If those contacts become a problem, I can simply get rid of the spam or other by deleting that alias.)