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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.
It's possible they turned basic auth off on your account (at least temporarily) - they are turning it off and on so users get the hint that it is going away before it is shut off for good.
Well, isn't the authentication only for two factor logging in? I'm not using that. I did test it, as noted earlier in this thread (which has gotten fairly long), but that did not solve the problem. Even so, if they did turn it off, at this point, it would not be something you could say was temporary, it's been many months now.
They are allowing me to do this with my main account only, not any of the aliases. I am presuming the reason they are not taking the settings is because they have decided not to allow any aliases to do that anymore.
Well, isn't the authentication only for two factor logging in? I'm not using that. I did test it, as noted earlier in this thread (which has gotten fairly long), but that did not solve the problem. Even so, if they did turn it off, at this point, it would not be something you could say was temporary, it's been many months now.
They are allowing me to do this with my main account only, not any of the aliases. I am presuming the reason they are not taking the settings is because they have decided not to allow any aliases to do that anymore.
2FA helps protect the account when logging in - but if the service does not support modern auth ( oAuth2 ) you need to use an app password if 2FA is enabled. When they disable basic auth in September, Microsoft will be removing app passwords too. Only services or apps that use modern auth will work. - which means you won't be able to use the accounts in google (unless google updates the service).
Their gmailify service supports modern auth but it only allows one account to use it.
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I've gone and turned on the 2FA and created the app pw on the outlook account (hotmail account). However, I still cannot send email on the outlook email via my gmail account.
Gmail "send mail as" settings are as follows:
SMTP server: smtp.office365.com
port: 587
username: full email address
Password: app password
Connection: TLS
Error Message: Authentication failed. Please check your username/password.
Also tried SMTP server: smtp-mail.outlook.com
as well as app password and my email password for both SMTP settings, all ends up with failed authentication.
P.S. smtp.office365.com was the SMTP setting which worked up until maybe the beginning of this year before it ran into sporadic issues.