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.

Thank you, Xephyr. But ...

I see you have passwordless account turned on.  I don’t.

I note, I’m not talking of using it from a cell phone, I use it on a desktop.

I tried turning off and then turning on Two-step verification. Oh, gee, I had to go through an entire setup just to set a two-step verification. And it produced a very long string — 25 digits long —  of security code I’m supposed to remember — not possible, not anywhere near that long — and store somewhere to use when needed! That’s insane, I cannot have to find that and use it. If that is how they handle Two-step verification, I can’t use Two-step verification, I would never be able to get through it. I can’t have to be finding and putting that code in and from every device or machine I try to login on, which won’t necessarily even by my own. 

My Two-step verification was marked as turned on when I started. If I ever set it up before, and I was supposed to have that long string, well, I don’t even recall needing that long string, I have no idea where I might have saved it -- it is not reasonable to use. It's not a code they will send me, it is a code I'm suppose to know, 25-digits long! 

I can’t be putting that code into the setup for Gmail to use as the login password! That can’t be right, it's not my login password. I’m not changing my password, and Gmail still needs that. It seems I also now will have to turn off two-factor verification, that is the most unusable version of that I have ever come across.

I just ran a test, so logged out of my Hotmail account and then I logged in again. I did not have to do that two-step verification, only used my password. Huh? Then what is that code for? And how could it be usable by Gmail? It's not instead of using a password.

What is this two-step verification if it doesn’t even come up when logging in?! How is it going to thwart any hacker if it isn't even used?! Are you saying that in Gmail, instead of putting in my Hotmail login password, as it asks for, I instead put in this 25-digit two-step verification code — even as it is not used for logging in?! That is NOT the password for my Hotmail account. That 25-digit code would be use AFTER using my Hotmail password. How can it skip the password and just use the 25-digit verification code?

No matter how I look at this, it seems completely out of line, Microsoft has gone off the deep end coming up with something like that. That code must be something someone at Microsoft came up with in the middle of having a stroke. 

Again, there is absolutely no place I can store that code and ever have the slightest idea of where to find it if I need to use it, nor even remember in another month that I ever had such a code. It is 100% unusable.

Once 2-step verification is on, check to see if App passwords shows up on the menu mentioned. If it is, click Create a new App password. It should give you an approximately 10 character password, which you can then copy or type into the gmail smtp login settings. This is what worked for me case, cannot say if it'll work for you as well.

Passwordless account is not turned on for my account. The screenshot specifically shows "OFF", and an option to turn it on, so this should be completely unrelated to the issue at hand.

The 25-digit code it gives you is a backup in case you ever lose access to your authenticator and need to log back into the account. Just something to keep safe in case you switch/format/lose the phone the authenticator is on, this has been the case for every 2FA I've used.

Thank you.

First, now that I go into those settings again, at the Security page, it no longer lists Two-step verification at all, on  

or off.

When I then click into “Manage how I sign in,” then I see Two-step Verification, and it says it is on. (I still have not had to do any two-step verification when I log into my account.)

There are no app passwords listed there under "App passwords." So, I use the “Create a new app password hyperlink, and it takes me to a new page — “Use this app password to sign in.” That has the newly generated app password, and it is 16 digits. It does not list any prior app passwords I have generated, and every time I go to it, it generates a new one. It says I am to create a new app password — a different one — for each app or device. 

It says to put it in as password in my gmail.

But this confuses me. This is instead of two-step security. Again, my two-step security is not making me do anything extra or different when I login; I just put in user name and password,  and I’m in. So, why would it matter that the gmail setup can’t do two-step verification?  

I just tried putting in that new app password in the gmail setup. It would not take it. I got this message:

“Couldn't reach server. Please double-check the server and port number.”

The SMTP Server I have in is: hotmail-com.olc.protection.outlook.com

The port number is 587.

Hi @Xephyr

Yes, you are correct.

You don't need an "App Password" unless you have Two-Step Verification enabled. So I assumed, anyone who lands here, should already have the two-step verification enabled otherwise you can just use your regular password without having the issues "two-step verification" users are having with authentication.

Glad it's working for you now!