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App-specific Password not working

Trying to log into my iCloud email through the New Outlook. log into iCloud, generate a new app-specific password, copy generated password into Outlook.....Outlook say its incorrect..


Rinse, Repeat 3 times. same thing

Windows, Windows 6

Posted on Oct 17, 2023 5:58 PM

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Posted on Nov 14, 2023 11:32 AM

I am having the same issue. I was having an issue with iCloud syncing with Outlook. Removed my iCloud account from Outlook. Restarted Outlook. Revoked the prior app-specific password. Generated a new app-specific password. Tried to connect Outlook and my iCloud account both with the account syncing to Microsoft and a direct sync to iCloud. In both cases, the log-in screen returned an error that the password was incorrect, despite copying and pasting. Tried three times with new app specific passwords. You referral to Microsoft Virtual Agent was unhelpful. They have no answers here.

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Question marked as Top-ranking reply

Nov 14, 2023 11:32 AM in response to TheLittles

I am having the same issue. I was having an issue with iCloud syncing with Outlook. Removed my iCloud account from Outlook. Restarted Outlook. Revoked the prior app-specific password. Generated a new app-specific password. Tried to connect Outlook and my iCloud account both with the account syncing to Microsoft and a direct sync to iCloud. In both cases, the log-in screen returned an error that the password was incorrect, despite copying and pasting. Tried three times with new app specific passwords. You referral to Microsoft Virtual Agent was unhelpful. They have no answers here.

Oct 17, 2023 6:23 PM in response to SpikeyFireStorm

SpikeyFireStorm Said:

"App-specific Password not working: Trying to log into my iCloud email through the New Outlook. log into iCloud, generate a new app-specific password, copy generated password into Outlook.....Outlook say its incorrect..Rinse, Repeat 3 times. same thing"

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Create an iCloud App Password:

  1. Go Here: Using App-Specific Passwords - Apple Support
  2. Scroll to: How to generate an app-specific password
  3. Proceed from there as necessary

Nov 14, 2023 1:07 PM in response to bflock

bflock Said:

"I am having the same issue. I was having an issue with iCloud syncing with Outlook. Removed my iCloud account from Outlook. Restarted Outlook. Revoked the prior app-specific password. Generated a new app-specific password.[...]"

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Try Creating and Using an App Password for iCloud Mail:

Go here, and see if this is of any help: iCloud: Using App-Specific Passwords - Apple Support


And for reference....

Other Common eMail Domains' Sites:

Nov 25, 2023 2:07 PM in response to SpikeyFireStorm

I, too, had my Outlook account rejecting messages due t0 authentication failure. I spent 5 hours on the phone today with Apple support, and finally trace my problem to this: a recent modification by Apple to iCloud defaulted a number of user settings. Years ago, I had originally had my iCloud email forwarded to my ISP, where I poll for all my other email accounts. To overcome security rejections from some sites, I stopped the mail forwarding, and just polled Apple's server directly. And, although I use Outlook, not Mail, the Mail account forwarding was mysteriously restored, resulting in my App Specific password for Outlook not being accepted by my ISP. I went into Mail settings and turned off the forwarding, and that fixed everything.


I hope this is helpful.

App-specific Password not working

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