App-specific Password not working

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.

So has anyone resolved this issue? I am now dealing with it... reset password multiple times, generated several app-specific passcodes, nothing is working. When I try to add account to Outlook, it rejects both the password and the app-specific passcode. I feel like I'm close, but it's been half a day wasted.

After hours of trying to figure this out, revoking & recreating app passwords it occurred to me that most apps do not like - in the passwords. I tried the app password w/out the - & it worked like a charm. so instead of aaaa-aaaa-aaaa-aaaa it would be aaaaaaaaaaaaaaaa

Exact same issue on my end - generated a new app-specific password to connect my iCloud email in Outlook, but keep getting an error message after entering the password in Outlook, no-matter if the password is copied/pasted or manually typed-in.

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

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:

• AOL: Create and Manage Third-Party App Passwords - AOL Help
• gmail: Sign in with App Passwords - Google Account Help - Google
• Outlook: Manage App Passwords for Two-Step Verification - Microsoft Help
• Xfinity: Two-Step Verification for Signing In and Xfinity App Setup - Xfinity Help
• Yahoo: Generate and Manage Third-Party App Passwords | Account Help | Yahoo

I've found that my pasting had entered hidden carriage returns at the end of the password entered into Outlook. Typing it in by hand and Outlook accepted the password.

This after creating new and then revoking those passwords.

Sounded like a good thing to check, but mail forwarding is not turned-on on my account. Glad you managed to get your issue sorted.

Can't believe that worked: manually typing the password.. wtf?!

SpikeyFireStorm Said:

"App-specific Password not working: yeah i know HOW to generate one. the problem is I take that generated password and Outlook says its wrong."

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Go Through Microsoft:

Use Microsoft Virtual Agent: https://vsa.services.microsoft.com/en-us/v1.0/

Report back any troubleshooting techniques you are provided with.

RyanAC588 Said:

“Exact same issue on my end - generated a new app-specific password to connect my iCloud email in Outlook, but keep getting an error message after entering the password in Outlook, no-matter if the password is copied/pasted or manually typed-in.”

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Take a screenshot of what message you are seeing.

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.

I had the similar problem and solved it by re-creating the iCloud account with a new app-specific password in Windows Settings -> Accounts -> Email & accounts.

Just entering the new app-specific password in Windows Calendar or in New Outlook did not work.

Tried again today on the off-chance that it would work.... success! I manually typed-in the password and it was accepted.

Not sure if this is the result of some fix published on the MS or Apple end, but I'm fairly confident that I'd tried manually typing-in the password before.