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Outlook 2016 desktop app - My Login credentials dialog box isn't appearing!

Sometimes when I start up my outlook Desktop app, I do NOT get a password prompt and, as a result, all I see are yesterday's email!  or the email from whenever the last time I logged in.

How can I nudge the login credentials dialog box to appear.  

I already tried shutting down outlook and starting it up.  That didn't work.

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FOX
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At the top of your outlook click Send/Recieve > Send Recieve All Folders
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Still no prompt for my login credentials. I tried "repair" using the MS Office installer program.

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Brian B
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What is the indication that you should be getting a password prompt? >>
My inbox does not have the most recent emails.  EVEN after I press send/receive.

I'm using MS Teams but I'm logged into my Teams account under a different name and domain.  Could Teams be messing this up?

Is the stats line saying "password needed"?
It says last updated 1/23 and DIsconnected.  but it's not disconnected.  I can access the web and check my email on any public mail site.
Check under the Send/Receive menu and see if there is a login button there.
No
Otherwise, go via Control Panel and delete your email profile and create a new one.
I want to avoid doing this.
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1. What kind of email account are you connecting to? Exchange, POP3, IMAP, or something else?

2. When you run the send/receive, does the status message change at all? Or does it just stay "disconnected" the whole time and not do anything (as if you didn't click the button at all) ?

3. Do you *normally* get a login prompt each day?

4. Do you run any kind of internet security software that has any anti-spam features? I ask because those kinds of things usually work by sitting between your mail client and the mail server and they read your mail as it comes in so they can flag it. If that software is malfunctioning in any way, it could lead to Outlook not being able to contact the mail server and thus never prompt you for a login, although you'd usually get an error message of some kind.
1. What kind of email account are you connecting to? Exchange, POP3, IMAP, or something else?
EXCHANGE

2. When you run the send/receive, does the status message change at all? Or does it just stay "disconnected" the whole time and not do anything (as if you didn't click the button at all) ?
Nothing happens. It's as if I didn't click the button at all.

3. Do you *normally* get a login prompt each day?
I do because i don't like caching my passwords on any email or shared drives.


4. Do you run any kind of internet security software that has any anti-spam features? I ask because those kinds of things usually work by sitting between your mail client and the mail server and they read your mail as it comes in so they can flag it. If that software is malfunctioning in any way, it could lead to Outlook not being able to contact the mail server and thus never prompt you for a login, although you'd usually get an error message of some kind.
Malware Bytes and the default Windows 10 defender app.  That's it. 
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Okay, so neither Malware Bytes and Windows 10 have any mail proxies, so the cause is unlikely to be either one of those, although when a problem could have a dozen different influencing factors, it's still good to be methodical about it and run a test where you turn them off like Brian said.

Just shut down Outlook, disable both Malware Bytes and Defender, and launch Outlook again. If it -does- prompt you for login, don't enter anything (you don't want to taint the results). Just close the prompt and shut down Outlook again and open it back up again for a second test. You can re-enable both after that.

Since you indicated that it acts like you didn't click the button at all, that sounds like Outlook is thinking it's working in Offline mode. Full disclosure - while I've used every single major version of Outlook ever released, I don't -currently- have a 2016 client on any of my workstations, so I'm going to use some references and screenshots from Outlook 365, which should be PRETTY close to 2016. There's a chance that a button may be in a slightly different place or have a slightly different label (Thanks, Microsoft).

So let's start with the simple stuff.

First, we need to make sure that the Work Offline button (usually in your Send/Receive menu) is NOT selected:

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It will be highlighted a darker color if selected. If that button is selected, it will not attempt to contact the server or prompt you for credentials! If you use any macros or assistive devices, or even you're just one of those people that knows and uses a bunch of keyboard shortcuts, it can sometimes be easy to accidentally select a button like this.

Second, go to your Send/Receive area and click the Send/Receive All Folders button (it's fine that it doesn't do anything - we're just triggering it). Then you should have a button called Show Progress - click that and you should see a progress popup.

If you don't see the Show Progress button, then just click on the little down arrow next to Send/Receive Groups and select the first inbox under your account name. That should trigger the progress window, as well. That process looks like this:
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The progress popup:

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Anyway, you'll want to take a screenshot of the first tab (Tasks) and the second tab (Errors) and share them here (just use Paint or something to erase or blur out any email addresses or names first).

And finally, the more "severe" step is to enable the debug logs for Outlook. This will capture a bunch of information, and it's usually a pain to sift through to find what you need, but it might be the next appropriate step.

To do this, you open up the Outlook Options menu (usually somewhere in the File menu), and then go to the Advanced section, and scroll down to the bottom and check the "Enable troubleshooting logging" checkbox. Then click on OK and do a full shutdown and restart of Outlook (make sure it's not just closed down but still running in the system tray).

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It's important to know that you don't want this checkbox enabled at all times, because otherwise it's just going to fill up your hard drive with debugging logs that you don't need. And ideally, we only want logs that cover the timespan of the problem. So once you've restarted Outlook, trigger the Send/Receive again, wait about 1 to 2 full minutes, then go back to the options and uncheck the Enable troubleshooting logging checkbox, click OK, and close Outlook.

The log files themselves can be in one of 4 places within your temp folder, but the most likely place is in %temp%\Outlook Logging. So open up Windows File Explorer and in the address bar, type in %TEMP%\Outl and you should see the auto-suggest popup below come up with the full "Outlook Logging" folder name if it's there:

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So go into that folder and just take a screenshot of the list of filenames. My guess is that you'll probably want what's in the OPMLog.log file, but it will be useful to know what files are there. DON'T attach any of the files here or share their contents yet. Let's first see what comes out of all this and then we can figure out the best next steps.



Checking to make sure you saw my last comment. Have you had a chance to try any of the steps?