Settings for using Outlook/Hotmail SMTP via Gmail

Shouldn't need to change password, but for me, I needed to add an authenticator for 2FA for the relevant App Password section to show up. After clicking "Security", then "Manage how I sign in", should be able to see something like this if the relevant Two-step verification settings are correct:

If your Two-step verification shows ON but "App passwords" doesn't show up I would probably suggest trying the age old "Turn it off and on again?" troubleshooting method.

I was already using Google Authenticator on my android phone for other purposes so it was simple to scan the QR code the webpage provides with Google Authenticator to add Microsoft's 2FA info to it, but I assume other authenticator apps would work fine as well.

Just for reference, even with two-step verification on, you can choose to remember a machine in order to not need it every time you log in. Plus, the point of App passwords is specifically for them to generate a random password for you to enter on devices that don't support 2FA at all, so don't need to worry about needing to make a new password or needing to relogin every time.

So, you are saying we have to change our password? Or can we just set our current password up again? I hope I can keep the current password, just set it up fresh.

Secondly, you say we must have Two-Step Verification turned on. Then do the password step. Will we need to leave it on? Won't that interfere with this working because the second step of verification has to be done manually every time? What is the second verification step, maybe a msg sent to e-mail that has a security code, or a text with that to a phone number?

EDIT: Wait a minute. I suppose I should have checked my settings before posting that. 

I followed you steps. All was how you listed until I got to #4. Once in “Security,” I have no “Advanced Security Options.” However, I do see I already have “2-Step Verification” turned on (but I never have to do a verification other than my password when I log in) — at upper right. I do see to it’s left a hyperlink to “Change Password.”

All that is down below is either “Data” or “Devices.” I looked into “Devices,” but there are none listed there, no gmail there. I alternately clicked into “Manage how I sign in,” nothing there to help, although I see some info there under “Enter Password” that would normally be used for 2-Step Verification. Again, it indicates I have that set up, but I never have to do that when I sign in. I think that is for if I need to verify my account if I need to recover it. 

That said about #4 not following what you said, I can still do #5, Change Password, using that language, not under “App Passwords.” I just checked it out, it will not allow me to use the same password, I have to change to a new password. I don’t want to do that - unless I were positive I could then go do that again to change back to original, which you can do with some places but not others. Microsoft might be one of those that will never let you change to a password you ever used before. 

As per my immediately above query, I would rather not change my password.  

Any input?

1- login to your hotmail account

2- click on your name top-right corner then go to My Microsoft Account

3- click on Security left hand side

4- click on Advanced Security Options

5- Scroll down to the section where it says App Passwords then click on Create a New App Password

That's it. Now copy paste that password in your gmail settings (for your hotmail login) with the settings previously mentioned.

For posterity, this finally managed to work for me after troubleshooting this off and on for several months.

However, to get "4- Advanced Security Options" to even show up, your account MUST have Two-Step Verification turned on, otherwise nothing of the sort even shows up in the Security Options page. Once 2FA is properly set up, the Advanced Security Options and App Passwords section of the menu will appear and everything should be smooth from that point on.

Thanks for that. I'll look into that when I can get to it.

Re password, yes, I'm not doing this from an app from Hotmail on the Internet. I know my Hotmail password. That has been and should be the password to use. I don't want to change my login password, and if I do, I can't get it back. IfI even have that setting in Hotmail, maybe I can try to put in my Hotmail password. But I think it woud already be in there, my login password.

What error message do you still get when you try to save your hotmail smtp settings on gmail? If it's similar to mine (wrong password), try the settings I mentioned with checked "treat as alias" & copy paste your app password that you can create from your hotmail settings (super easy to create one).

I think gmail is treated as "app" even though you're doing it form the web.

If you choose to try app password, here's how you get it:

1- login to your hotmail account

2- click on your name top-right corner then go to My Microsoft Account

3- click on Security left hand side

4- click on Advanced Security Options

5- Scroll down to the section where it says App Passwords then click on Create a New App Password

That's it. Now copy paste that password in your gmail settings (for your hotmail login) with the settings previously mentioned.

PS: I totally can relate to what you mentioned regarding little tasks becoming projects! Lots of that in my life too. All we can do is take it one step at time.