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Bwder's avatar
Bwder
Copper Contributor
Aug 22, 2025

Passkey on iPhone app disrupts desktop

I am running Outlook 2019 desktop. I use the Outlook mobile app on my phone. Recently, I was prompted on the phone to create and run a passkey. Thinking I would be able to input the passkey into the desktop version, I went ahead. However,"

1, there is no option to input anything. (see screen shot)

2. I have repaired the desktop via the control panel

3. When that failed, I reinstalled and activated the license. There has been no change.

4. I have deleted the passkey on the iphone app and gone back to password. Still not any change.

5. I am being locked out of the desktop as it keeps trying to sync, so can only work on this so long, without repeating errors.

6. I reset the password through the online Microsoft trouble shooter. Still no luck. Locked out again.

7. In addition, since I reinstalled the software, I keep getting the countdown dialogue box telling me to activate the software package (including Word, Excel, etc.). I have activated it four times, and am just watching the countdown to 30 days when eventually, I assume, I will be locked out.

8. Furthermore, upon resetting the password using the online troubleshooter, it created a whole new live.com sign in erasing my old user community profile along with it.

Is anyone else having this kind of problem? How to rectify by getting rid of the passkey, since there is no sign in availability with Outlook 2019?

Thanks for any insights and help.

2 Replies

  • Bwder's avatar
    Bwder
    Copper Contributor

    I wanted to respond with a "thank you," as it will be a bit of time until I can carve out space to do this. Will keep you posted.

  • Not sure this will help (fairly long description) but you have 4 different types of email accounts and 4 different levels of security on each. From my experiences helping clients with Outlook and iPhones for 15 years, they don't rely on each other for adding accounts, so something else is going on.

    My simple answer: Create a new Outlook profile, do not delete the current one. Add each account and then follow my instructions for security below. I added both/Outlook and iPhone. Then after Outlook is setup, do some testing of send/receive to make sure it all works, then go back to the Outlook app and see if all are getting those emails you just tested, reply back. Setting up accounts should not require all the work you did with the software/reinstalling, etc. 

    **Outlook desktop for those accounts**

    --Hotmail, in general might have security on it or not. If you want to test it, log in on incognito and then log in and see what security is prompted. 

    --365 Exchange, might not have security on it either, MS is forcing it lately so it might and that would use most likely the Microsoft Authenticator app. Hotmail does not use that app as far as I know. 

    --The Gmail has security, an "app password" will be needed for your version of Outlook (I believe) and or you will be prompted to log in on Chrome to allow the Gmail to connect, but I don't think you will see that option with your version. You also might see a 2-step authenticator requirement, so you have to turn that on for you to use as app password. 

    --The last email is IMAP with Google Workspace and the same security applies as regular Gmail. 

     

    **iPhone for those accounts**

    --iPhone now might require you to use your phone password (passkey) for businesss 365 accounts/Exchange (the only time I have seen this anyway) and that is not connected to Outlook desktop at all. Only for the phone. So for each account you add to your phone, you might have to put in your phone password/passkey for security. And now iPhone can make you wait an hour for Microsoft 365 Exchange accounts (your 2nd in the list). 

    --Gmail will ask for some type of security when you add to the iPhone, usually 2-step or maybe nothing. It might redirect you to a browser to login and approve it as well. 

    Posting this for others to learn a bit too, 

    Lisa