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I have a few e-mail accounts, all online rather than desktop application, for differing reasons – no, none for anything dishonest or malevolent, not for spamming, nothing negative. And I normally use a gmail account to handle my Hotmail e-mail, and Outlook e-mail. (I have a couple extra account names I use in Hotmail, one is an Outlook name. That is, the e-mail to my Outlook name will come into my Hotmail account, as the Outlook name is effectively an alternate name for my Hotmail account. This is something you can do in Hotmail settings).
Mail coming into my Hotmail account automatically goes over to my Gmail account. When an e-mail originally comes into my Hotmail account using the Outlook name, it is moved over to my Gmail. When I respond to it from gmail, it will go via my Hotmail account using the Outlook name. That is set up in gmail, via SMTM (just like from a desktop e-mail client, which is what I use my gmail as, as my interface for Hotmail, because I find gmail preferable).
OK, now to the point. In recent months, when I get an incoming e-mail in my gmail account from my Outlook (Hotmail) account, and I try to respond to it, it is sent back saying it can’t connect, says I need to check my SMTP settings. Well, I have checked, and I checked to see if Hotmail/Outlook changed them since originally set up. My settings are exactly what Hotmail/Microsoft says they should be.
SMTP server: smtp.office365.com
user name: (that is the Outlook e-mail address)
password: (correct)
Port: 587
All that matches what Microsoft/Hotmail instructs to use.
But there is a problem. Any ideas?
Configuring preferences and options in Outlook.com
Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.
Don't use smtp.live.com -you need to use smtp-mail.outlook.com now. They changed it from smtp.office365.com recently.
POP, IMAP, and SMTP settings for Outlook.com - Microsoft Support
Well, David, if you are with Microsoft, maybe you can put the word through to whomever needs to hear it to please do not make such a drastic change, leaving us no way to use the service. Even using 2FA does ont solve th eproblem. I only use gmail as an interface for my Hotmail account -- because the gmail interface is much smoother. At first, it was faster, but over time as thigns have changed, it remained better. For instance, now, the way Hotmail uses its spelling correction within an e-mail, it inteferes with me trying to make corrections! Gmail does it so nicely.
But another thing, doing things as I have been for decades now provides me a backup for my Hotmail account. In fact, I accidentally deleted everything in my Hotmail Inbox last week. But I have it all backed up in Gmail.
Doing this undermines me, and the various others in this thread, and I'm sure many not in this thread. Blocking this for me might force me to abandon Hotmail!
I spun up a lightweight SMTP server at https://sendas.email for myself to solve this problem, but decided to open it up to the world.
You can also run your own docker container https://github.com/blacktirion/email-oauth2-proxy-docker but managing, maintaining and keeping the certs up-to-date can be kind of annoying.
There are a few Google community posts regarding this, essentially the ball is in Google's court to implement a better sign-in method for Outlook users:
(I imagine there are more results if you also include hotmail, microsoft, msn, etc.)
Threads:
It's not just a Gmail issue however, disabling of basic authentication (which, ultimately, should not be a bad thing) is impacting anything using a 'legacy' setup, including printers lol: https://stackoverflow.com/questions/79001719/535-5-7-139-authentication-unsuccessful-basic-authentication-is-disabled-broth
Thank you Vince. I will answer your questions, etc, but first, I see you are providing a different SMTP setting than I was provided previously and using for years now. Actually, I was instructed to change to this SMTP setting from the one you are giving me. Hotmail/Outlook/Microsoft supposedly had changed what was to be used, decided all should go through office365. It harked worked fine for years now, fixed the problem of using live.com. This current issue seems to have started only in recent time, recent months. Do you know if Hotmail/Outlook/Microsoft has changed it back?
I am using: smtp.office365.com
You are saying to use: smtp.live.com
I will try that. But it will take some time before I can get word back from people to whom I send, so I won't have immediate results.
To your questions:
“•Can I know what is this desktop email client app that you are using?”: I am not doing this from the desktop, I am doing it from Gmail online.” I am using them as if they were a desktop client.
“•Is this also happening when sending/receiving emails in the Gmail.com webmail?” and “•Is this happening to all devices, browsers, and networks?” Yes, that is where it is happening, I do not use and desktop client. The people receiving the e-mail tell me later the e-mails are going to their Junk folder, or other times I get a message back that it was rejected. I can’t tell if that rejection is coming from Hotmail, or from the receiver’s e-mail. But it works fine if I instead send it direct from Hotmail. The people I am sending to normally get their e-mail on mobile, and they tell me there are no settings there (mobile) to protect e-mail from my address nor to make a rule to never send it to Junk. Coincidentally, two who have told me this are using Hotmail on mobile. So it can’t be fixed on their end. I am sending from Gmail, via SMTP through my Hotmail address from my computer, not mobile.
To clarify your first paragraph, I’m not talking of sending e-mail from my Gmail account to my Hotmail account. I am sending an e-mail to other people, from g-mail using the SMTP settings to send it through Hotmail so they get it from my Hotmail address. (I've been doing it that way for decades, originally just because Hotmail was slower.)