Settings for using Outlook/Hotmail SMTP via Gmail

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.

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.

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.