Outlook keeps asking for a password. Why?
Hi, everyone. Leo, note and boom here for
askleo.com. Let's get right into the question
"I have and use on occasion, Microsoft Outlook as a default email program.
when I go to use the program,
the login menu comes up asking me for my password in my settings.
I checked. Remember password.
I click
Okay, and the damned thing keeps coming back and back and back each time I click.
Okay, how can one stop this? After about a dozen or so clicking on
okay, it will leave me alone for a short while."
Yeah, that's Outlook's way of telling you that something's wrong.
It could be any of a number of things. I'm going to go through exactly what some
of those things are, but it is definitely the case where
whatever you're doing isn't what Outlook needs.
It needs something else, and it might be something in your email
account that you're accessing that might need to change.
Let's take a look at the most common causes.
First, the number one most common cause,
and I realize that most people don't want to hear this, but it's very true.
The most common cause you enter your password wrong.
It literally is a typo on your part or the caps lock key is on or something else
is going on that's preventing you from typing in the password correctly.
Now, again, I get that's frustrating to hear.
And since you only see like,
the dots or the asterisks as you're typing your password in,
the only feedback you have that it's the right password is your own keystrokes.
And if those are wrong, you would never know.
My recommendation in a case like this is to fire up an application like Notepad
and type in your password, make sure it's the password you think it is correct.
Any keyboard problems, any caps locks, problems, whatever else might be getting
in the way, but make sure you type it in correctly.
Then copy the password to the clipboard
and then go paste it into the password field.
That should work.
Now, if it doesn't, well, let me ask you a question.
Do you, by any chance,
have two factor authentication turned on for many email systems?
Two factor authentication.
Complicates this because many email programs do not have
the ability to properly ask you for your second factor.
So if you require two factor authentication and you're using a program
that can't do two factor authentication, the only thing that the email service can
do to maintain your security is to reject the login.
You weren't able to provide your second factor so you can't log in.
Now, outlook and many other email programs do a really bad job of telling you what's
wrong, because they were all designed and written before.
Two factor authentication was even
a thing, so they have no way to tell you that.
That's the problem.
The protocol doesn't even have a way to tell you that that's the problem.
So what that means, though, is then you need to do either of two things.
The easy solution is to check with your email service
and see if they support what's called an app password.
An app password is something you'll find
somewhere in your security settings for that email service.
So you'll have to go online.
For example, you have to go to Gmail,
dot com or Outlook dot com, or wherever it is, whatever email service
it is you're using, and you'll go there and in your security
settings, look for something called an app password.
It's usually referenced in the same place you happen to be in.
When you first set up two factor authentication, app passwords are unique.
They are generated not by you, but by the service.
They will show you your app password typically exactly only once.
It will usually be long,
like at least twelve, if not 20 characters long and completely random.
So it's not something you'd ever be expected to remember.
That password you would then copy and paste into the password field
of Outlook or your email program that's having this problem.
That password is a password that when used
to sign in by an application, not a user interface,
but by an application like Outlook, allows it to not need two factor authentication.
It allows it to log in without that additional requirement.
It's something that is secure because you had to go set it up.
You had to take this extra step to create
the app password, and it's not something that could be used at a login interface.
It can only be used in an application interface, like an Outlook.
In an ideal world, the reason it's called
an app password is that you might use or create a different app password for every
application that might need access to your account.
Typically, that's only one. That's fine.
But in the case where you use Outlook
and you use Thunderbird and you use Mclient and you use whatever else because
you're somebody that does that kind of thing, then you might have a different
password for each application if your email service provides it.
But that's one of the things that can happen if two factor has been enabled
on your account, and that's something to look for.
Now, what happens if you can't or the service doesn't provide
app passwords or it's just not a solution that you want to go down.
The other approach,
and this works with newer versions of many of the common email programs.
And I know that this now works with Thunderbird, and of course it works
with Outlook is what's called it's open authorization.
But what it is is rather than an email
program asking for your username and password when you need to authenticate.
Instead, it hands that job off to the servicing
question, so that rather than Outlook, the program asking you for your username
and password, you'll get a dialogue from, say, Gmail,
it will ask you for your username and password.
But because that interface is provided
by Gmail in real time, it's provided by Google in real time,
then it has the opportunity to ask you for your second factor.
And that way, when you say, Remember me on this device,
you're remembering it for that email program that then lets you truly log
in with two factor authentication in the application that you're going on.
Now, the problem is that what if you've
got Outlook configured for your Google account already?
The only way you can set this up is to set it up from scratch.
When you create a new account in Outlook that then accesses your email from Google.
At that time, it'll probably default to OAuth if OAuth is available.
I don't know of a way to switch an existing configuration in Outlook or
even in Thunderbird, for that matter, from the traditional username and password
to using this OAuth style of authentication.
So in those cases, you may be stuck trying to use an app password to be able to log
in without having to reconfigure your mail program.
But if you have the opportunity to switch, if you have the opportunity to configure
it up from the beginning, then OAuth is the way to go because it
takes the burden of authorization off of the email program and then lets
the service do whatever it might need to authenticate that you are who you say
you are and actually have the rights to access that email account.
Now, speaking of Google, there is one other thing in Google
that can cause it, and that is that again, because of this difference between OAuth
style of authentication where you hand off authentication to Google and they can do
whatever they need versus a traditional username and password authentication.
Google has taken the position
that username password authentication is, quote, unquote, less secure, and that is,
in fact the phrase you end up looking for in your Google settings by default.
Even if you don't have two factor turned
on when you try to log in using username and password on Google to a Google account
from a desktop email program like Thunderbird using username and password,
Google will consider that to be less secure and less secure.
Apps are disabled.
They're disallowed by default.
So in that case,
and this is specific to Google as best I understand it, you'll need to go to Google
and look for that allow less secure apps setting.
Once you have that turned on and Google
will warn you that it's less secure then and only then can your desktop email
program like, say, a Thunderbird actually sign in using username
and password when you don't have two factor authentication turned on.
That's one that catches a lot of people by surprise.
And it's one of those things where, yeah, if you know the magic incantation,
if you know the setting to switch, you can switch it.
But ideally you'd switch to OAuth which maintains all the security you want
without having to go and find this obscure Google setting.
Almost finally, in terms of common scenarios, your account could be hacked.
I hate to say it, but repeatedly asking
for your password is one of the first signs that your account has been hacked
and the hacker has in fact changed your password to something else.
Really, the only thing you could do
in a case like that is to then go to the account online and perform account
recovery to regain access to your account, change your password,
increase your security, do whatever it takes to get back into your account.
If your account has been hacked now, I do have a number of I'll just call them
less common possibilities assuming you've gone through everything that I've just
talked about and none of it applies here's.
Some other random things to look at.
The mail server itself could be having problems, in other words,
the Gmail or the Outlook dot com or the Yahoo Mail or the EarthLink or
whomever they could just be having problems.
And this is one of the ways that that could manifest.
Like I said, that protocol doesn't really have a lot of flexibility in terms
of being able to tell you exactly why your login is failing.
All it's telling you is that your login is failing without having a reason.
The server itself not working properly.
Could be one of those reasons if the email programs configuration is
wrong, meaning that the top three or IMAP settings you've entered for the program
are wrong or have changed underneath you or something like that.
That could lead to this.
If the SMTP server you've specified is
wrong or has changed out from underneath you.
That can also manifest as repeatedly
asking you for your password at some of the oddest times.
Actually, if you mistyped your user ID, if you got your own email address wrong,
which is surprisingly common, then that password won't match
with that user ID, and that user ID may not even be valid.
In which case it'll keep asking you
for your password because the login will have failed.
Your internet could be down or could be having problems.
Typically, if it's down, you'll get a much clearer message from your email program.
But if there's some hiccups going on, if there's problems with the connection
between your machine and the email service that could indeed be responsible
for something like this, it's possible that in some cases
a firewall could be blocking your access to email services.
This happens, for example, in places like hotels and so forth.
If you're in the same place, this is unlikely unless you've been making
changes to your firewall or your network configuration.
And of course, there's lots and lots
of other reasons that this could possibly happen as well.
But those are the most common,
the not quite so common, and then we'd be getting off into the obscure.
So hopefully this has given you some
things to look at, some ideas to look into.
Should Outlook be repeatedly asking you for your password?
There are lots of things that can possibly cause this symptom.
That's a reflection of just how bad that interface is.
All it's really telling you is that something went wrong.
It's not telling you what that something is.
Everybody assumes it's the password, but sometimes
for updates. For related links for comments and more,
visit askleo.com/4495 I'm Leo Notenboom, and this is
askleo.com. Thanks for watching.