Settings for using Outlook/Hotmail SMTP via Gmail

No worries, it's totally understandable. Like I said, I stood this up for myself but figured I'd see if anybody else was interested.

Essentially, the service is a TLS/basic auth SMTP server that's compatible with Gmail. It accepts a raw SMTP payload from Gmail and then shoves it directly into Microsoft's sendMail API (https://learn.microsoft.com/en-us/graph/api/user-sendmail?view=graph-rest-1.0&tabs=http#example-4-send-a-new-message-using-mime-format), which is why I need the Mail.Send permission. With OAuth, the service can access only what you allow it in the confirmation screen and you have the power to revoke the permissions whenever you want. When you auth, it generates a random password (similar to the app-password system) that you can use in Gmail:

If you want to do it yourself, you can use https://github.com/simonrob/email-oauth2-proxy/ as a starting point. You'll need to setup a server with a domain name + SSL certificate so that Gmail can communicate with your server securely (let's encrypt is free for that https://certbot.eff.org/).

<Removed-CoC>

I ran into this exact issue. I found Gmailify to be way too heavy so I created https://sendas.email as a solution. It works by presenting a compatible SMTP server to Gmail and sending the mail through the outlook.com API (using the exact SMTP payload, no modifications).

My alias just stopped working a week ago.

Keep putting in the correct information and can't get it to work. I'm still get my hotmail emails forwarded to my gmail account, but I can no longer reply as an alias from hotmail.

I can reply. It just reply's from my gmail account.

ggrrr

That is definitely due to the change from basic to oAuth2 -Gmail's POP doesn't support oAuth2. If you remove the account and add it as a gmailify account, it will work. (I recommend letting Gmail pull in the mail instead of forwarding.) The only limitation with gmailify is you can only link one account using it.

My alias just stopped working a week ago.

Keep putting in the correct information and can't get it to work. I'm still get my hotmail emails forwarded to my gmail account, but I can no longer reply as an alias from hotmail.

I can reply. It just reply's from my gmail account.

ggrrr

Well, thank you. Vince, for the suggestion. But I'm not clear what you are getting at. There is no app involved here. Were you thinking I'm doing this from a cell phone? No, just from my computer. Your link suggests their would be a place in the "app" to do this; there is no place in my hotmail online to do this, and ot in Gmail.

I think you are suggesting using needing a passwork to open the app on a cell phone, and you are saying to try that. And that if it goes to the app, the app does only one thing, dispalys the e-mail. No, I'm not using an app. It's gmail online from a computer, to hotmail, which of course is online and I use it from a computer.

Related, I have told my friends with the problem, who are having trouble in Hotmail from a cell phone, to go to their hotmail onnine,a nd in there using settings to set a rule to never send e-mail from my address to Junk, and to protect my e-mail address, rather than block it. They tell me those settings are not in Hotmail on the cell phone app. But try to get anyone to do that. Bottom line, though, is that my address should not be getting sent to junk, and it should not be getting blocked. A special setting or rule should not be needed. I had to think the SMTP setting might be why it is sent to junk.