Settings for using Outlook/Hotmail SMTP via Gmail

Anonymous
2024-02-04T05:47:47+00:00

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?

Outlook | Web | Outlook.com | Settings

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  1. Anonymous
    2024-09-24T14:08:19+00:00

    I’m where I was before September: I can send from Gmail but under my main Hotmail account only, not the few aliases for that, all @outlook.com account names. 

    I have not messed with the settings in Gmail for the main Hotmail account. That uses SMTP server as:

    hotmail-com.olc.protection.outlook.com

    And the port is 587.

    And ”Secured connection using TLS.”

    I am unable to set up the Outlook aliases to actually work from gmail as it used to before early this year. But nothing about that changed come September. I tested 2FA previously, it did not solve the problem. I have never used the Outlook app on my cell phone other than to test the 2FA. I use Outlook and Gmail from my desktop computer. 

    I doubt this info helps anyone at all. But thought I’d throw it in there, as there were suggestions it might stop even for my main Hotmail account come September. Fortunately, it has not.

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  2. Anonymous
    2024-09-24T14:21:26+00:00

    Hi Me1004, I just wanted to drop in and say I do fully expect this to stop working because it looks like the gmail web setup that was being shown in this thread is not using Modern Auth. The changes for the basic auth deprecation are still rolling out. We have completed about half of the accounts at this point and will likely be done in the next 2 weeks. So I fully expect this to not continue to work much longer.

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  3. Anonymous
    2024-09-24T14:46:02+00:00

    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!

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  4. Anonymous
    2024-09-25T11:49:47+00:00

    I didn't realise how I use my outlook e-mail account was such an edge case!

    Is there no way at all to use an Outlook e-mail address in the Gmail web client any longer?

    All solutions I am seeing are saying to change Exchange settings re: Basic Authentication, but those only apply to company/enterprise accounts, not to Personal Microsoft Accounts.

    I have Gmailify set up, but that only allows me to check my outlook e-mail, not send from an outlook.com e-mail address. only became aware of this about an hour ago when I tried sending an e-mail from my outlook account via the Gmail web browser client today, received a bounce back error telling me to double check my SMTP settings. Using these settings both as alias and non-alias:

    • SMTP server 'smtp.office365.com'
    • Port 587
    • my full e-mail as my username
    • and a newly generated app password
    • Secured connection using TLS (only option is this or SSL)

    I get the following error:

    Authentication failed. Please check your username/password. <br>Server returned an error: "334 ... Authentication unsuccessful, basic authentication is disabled. [...] , code: 535

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  5. Anonymous
    2024-09-25T15:29:58+00:00

    What is "basic authentication?" Is that when you are not using 2FA? And under the new system, you must use 2FA? Gmail forwarding is not set up to handle 2FA?

    Is there no string we can use in the SMTP Server line or the Password line in the Gmail settings that will provide for doing the 2FA -- like putting in two passwords, the first, then the second that is the 2FA input, a certain delay between the two? I suppose that might depend on what is needed for the second input for 2FA.

    Has anyone checked if there is a similar thread at Gmail about this issue?

    I saw in another thread here that there was a similar issue back in 2013, although that one was using Hotmail as the interface for Gmail, the opposite. All these threads tend to point you to more and more links, and before you know it, you have 10+links open in diffent tabs and can't possibly follow them all. (It actually helps to give a final consolodated answer in one thread, in order to avoid too many tabs open to follow. It might be a longer post, but it's not confusing.)

    There must be something to do to solve this. Has anyone notified Gmal about it?

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