Apple Mail (iCal) OS X v10.6.8 authentication errors after 2-factor authentication for 3rd-party apps went into effect 6/15/2017

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Level 1

16 points

Apple Mail (iCal) OS X v10.6.8 authentication errors after 2-factor authentication for 3rd-party apps went into effect 6/15/2017

At approximately 3 PM (PDT) 6/15/2017 Apple Mail and iCal in OS X v10.6.8 began displaying errors when attempting to authenticate connections with Apple's servers to check iCloud/Me account email and when synching calendars.

Apple Mail when "getting mail" pops up saying "Enter Password for Account "x@mac.com". The xxx-IMAP server “mail.me.com” rejected the password for user “x@mac.com”. Enter your password again or cancel."

Doing as prompted the password Mail returns with..."The IMAP server “mail.me.com” rejected the password for user “x@mac.com”. Enter your password again or cancel."

Repeated attempts entering the (known-to-be-correct) password return the same error.

Similarly when trying to send a new message via Mail a dialogue appears that says "The SMTP server “smtp.mail.me.com” rejected the password for user “x@mac.com”. Enter your password again or cancel."

Repeated attempts entering the (known-to-be-correct) password return the same error.

iCal displays a dialogue box that states "The server responded with an error. The server did not recognize your user name or password for account “x@icloud.” Make sure you enter them correctly." Clicking on OK button dismisses the dialogue.

Bottomline: Has Apple overlooked how implementation of the 6/15/2017 required 2-factor authentication is going to impact end-users using genuine Apple Mail and Calendar programs that were configured using the @me.com server suffix?

Message was edited by: hanjive Is there a known work-a-round?

Posted on Jun 16, 2017 10:20 AM

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Answer 1

Jun 16, 2017 11:14 AM in response to hanjive

Hi hanjive,

This is a well-formulated question relative to the new security regime implemented on June 15th: has it been anticipated how this might/would/could affect "genuine Apple Mail" and other Apple app users? This reflects my own experience. Suddenly yesterday evening I get the pop-up message in Mac mail (the built-in app on my iPod Touch) to the effect that my "user name or password" is incorrect. Since then: no emails can be received or sent. I gather there are others in this boat as well.

I did receive the email notification on June 12th from iCloud re: app-specific passwords being required to access iCloud data using third-party apps. But, my current problem (and yours) apparently relates to the impact of these changes for existing Apple users.

I currently have an outstanding case file open about this, which is being handled by an upper tier supervisor who said she would be in touch with engineering staff. There was a suggestion that the two-step verification process might be needed. Hopefully I'll get a call back by tomorrow morning. Will try and post the response here.

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Answer 2

hanjive Author

Level 1

16 points

Jun 17, 2017 5:44 PM in response to hanjive

I can see how it (two-step verification) will "kick-in" (be invoked) when logging into iCloud via web-browser - not sure how it would work (or can work) using Apple Mail or iCal programs. All of that said I'm gonna go thru the steps via web browser now for one of my iCloud accounts.

Holy guacamole folks - gratitude to the contributors [vortex307 & Eric Root) who, albeit subtly to me, hammered home via shared links that there is a DIFFERENCE between "two-factor verification" and "two-step verification" - the latter of which, when configured properly, returns full functionality to iCloud accounts in Apple's proprietary programs [Mail and iCal) running in OS X v10.6.8.

Steps I took to resolve "key issues" of the OP: Using my MacPro running OS X v10.6.8 & compatible Google Chrome web-browser, navigated to https://appleid.apple.com/#!&page=signin to manage a primary AppleID. Turned my focus immediately to the Security section and invoked using "two-step verification" [might have relied on link within the "Two-step verification" hyperlink in prior replies to by-pass "two-factor authentication"]. After ±20-mins of fumbling to set up the "two-step verification" protocol [which included verifying six (6) iOS devices] - I next (KEY-Step) generated App-Specific Passwords for Apple Mail and iCal and then after copying/pasting those App-Specific Passwords in the respective programs for the iCloud account that "seemed broken" - everything is back to the way it was prior to ±3-PM June 15, 2017.

In hindsight - had I not ignored mention of "two-step verification" after it was first introduced (?2015?), I would not have reason to have erroneously assume that the implementation of Apple's 2-factor authentication on June 15, 2017 left users of 'legacy OSes/program" with iCloud accounts behind.

For the record - the issues in OP have actually been RESOLVED/SOLVED.

A postscript note - when configuring an Apple ID as above requires too many preliminary changes (new/revised security questions, etc), the system may place a temporary "hold" on the account before enabling two-step verification.

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Answer 3

9MacLS

Level 1

21 points

Jun 18, 2017 3:41 AM in response to hanjive

Hi Hanjive,

I had this same problem like many people which effected after 15 Jun, keep getting rejected password, so I decided the delete the account from my Mac Mail.app then tried to add it back as suggested as per this discussion in this link To Manually Set iCloud mail on 10.6.8 First attempt, I got all my email back and can received email inbox but I can't send out mail. I've tried all everything change port number and still can't send the email, then later in evening both incoming and outgoing mail not working and keep getting rejected my password error message.

Today I found your comment and I just click on all those link to read all information and click in to the link "two-step verification" and sign in my apple ID in Manage Apple ID page, and got alert same as you posted that I have to wait and do it after the date listed on my alert email.

During the waiting time I can do the generate app-specific passwords, I have a few question as below and if you could explain more in detail how you did it that would be greatly appreciated.

1. I already added back my @mac.com email account to Mail.app again but the account is still dimmed, not working, can not receive/send out email. I am using Macbook Air OSX 10.6.8 Snow Leopard.

So, after click generate the Password from app-specific passwords, do I just copy and paste the password in the password section of the incoming/outgoing server ?

2. Or I have to start over again, delete the account and add it back and put in on when I first adding the account process?

3. Should I use the new advised iCloud IMAP server as the previous post suggested (same as shown in my attached picture) or you did it fine with the original server mail.me.com and smtp.me.com ?

4. As it said "app-specific password", I believe this "generate password" should be used for each apps only and it shouldn't effect to my email in other devices iPhone 6 (10.1.1), iPhone 4s that currently I can receive/send email fine, right?

Thank you.

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Answer 4

9MacLS

Level 1

21 points

Jun 21, 2017 3:20 AM in response to Winston Churchill

I reqeusted Two-Step Verification and I even received email confirm about Two-step verification the period I have to wait which today I receive another email notify me that I can log in now to set up. But once I go to the security page the Two-Step Verification is not there instead it show Two-Factor Authentication.

By the way, I have another email account which is not connected with iclould server or never use with any APPLE ID, this email using it's own domain server POP, I can use it, everything working fine with mail.app only @mac.com account that right now having a problem with mail.app

This email is to notify you that your waiting period has ended and you can now set up two-step verification for your Apple ID (•••••@mac.com).

Please sign in to your Apple ID account page at https://appleid.apple.com, go to Security section to complete setup. For more information, read the FAQ.

If you did not attempt to set up two-step verification or you believe an unauthorized person has accessed your account, you should change your password as soon as possible from your Apple ID account page athttps://appleid.apple.com.

For your security, this automated message has been sent to all of the email addresses on file in your account.

If you need additional help, visit Apple Support.

Apple Support

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Answer 5

9MacLS

Level 1

21 points

Jun 21, 2017 4:21 AM in response to 9MacLS

Also, I have not yet turned on Two - Factor on my iphone6 or iphone4s. I never request or turn it on.

I access to apple id page through Chrome bowser or Safari from my Macbook Air which in security page it doesn't have any where to click to turn on/off Two-Factor, only the link Get start and after I click it, it just shows the detail How to Turn On Two-Factor on other compatible devices which I believe the reason it doesn't have turn on/off on the main apple id page because my computer version (10.6.8) is not compatible for Two-Factor. It's said at the bottom that " Don't have any compatible device, You can still get ......... (Learn More). Once I click learn more, it will lead to the information about using Two-Step-Verification instead which that where I get started the request Two-Step Verification by clicking Set up two-step verification now from that page.

I called local apple support here where I'm at, they said they combine Two-step verification in Two-factor and have me tried to turn it on and see if it works. I think I will wait and tonight I will try to reach apple senior advisor in the US, the guy I spoke with and reported him the problem and see what he will suggest because I told him after the waiting-period time of 2SV end I will call him and we try to use app-specific password on mail.app

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Answer 6

hanjive Author

Level 1

16 points

Jun 21, 2017 9:06 AM in response to hanjive

Just to be clear - the OP in this thread is about authentication (sign-in) errors encountered beginning on 6/15/2017 on Mac's running OS X v10.6.8 when using Apple's Mail and iCal programs to access iCloud account(s) data. Enabling two-step verification (2SV) online within AppleID management and then getting/using App-Specific Passwords (A-SP) in Mail and iCal solved the issues for my two (2) AppleID(s) and apparently for at least one additional contributor to this thread. Some folks in this thread running OS X v10.6.8 that use Apple Mail to access their iCloud data report having no issues since 6/15/2017 - lucky ducks*.

MacLady's stated solution pertains to Mail on a Mac running OS X v10.8.5 as suggested by an Apple Support technician which - in part - was to insert a sever-specific id (pXX-) in front of the incoming mail server string. Side-note: A corresponding pXX number varies across iCloud accounts. For example, the pxx number for incoming mail server in Mail on a Mac running OS X El Capitan is p24. One of the ways to determine a corresponding pXX for a specific iCloud account - login to iCloud then open Activity window (Safari) which shows the full server paths you are accessing at the iCloud website. (IMHO, respectfully, any further discussion about this might best be had in a NEW/separate thread.)

* For those with similarly configured systems that are experiencing the issue(s) described in the OP, suggest you enable two-step verification and then generate/use App-Specific Passwords. Keep in mind that if the 2SV and App-Specific Password solution doesn't work for you OR you do not like the overall functionality that is 2SV, you can always disable it.

Two-step verification for Apple ID - Apple Support

Once that page is loaded - scroll down to the sub-heading "How do I set up two-step verification?" where you will find a hyperlinked string of text "Set up two-step verification now" that ioads the URL below:

https://appleid.apple.com/manage/security/2sv/enrollment

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Answer 7

hanjive Author

Level 1

16 points

Jun 21, 2017 12:06 PM in response to 9MacLS

I can receive all my email back now. However, the outgoing mail server said Offline.

Double check that your outgoing mail server settings are correct.

You need to use the App-Specific Password in the outgoing mail server "advance" tab.

Mail > Preferences > Select iCloud account from list on left > on the right below Outgoing Mail Server (SMTP) pop-down > Select Edit SMTP List > select the one you are checking. Click on the "advanced" tab. The User name should NOT include @mac.com. Just the part before @mac.com. Paste App-Specific password there. Use default ports is selected and Use SSL is check.

As noted in graphic I have a couple different settings in the actual outgoing server name field - see graphic. Stick with whatever is already there - Just change user name, password click OK, close preferences and be sure to SAVE settings changed. Delete/trash any "items" in the outgoing box that were quened. Create a new email and test.

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Answer 8

Jun 16, 2017 4:50 PM in response to NateDigityDawg

Hi NDD,

Your situation is rather different, I think, owing to your use of Thunderbird so it looks like you will need to use an app-specific password mentioned by Apple in the June 12th email. Nevertheless, it seems these passwords may also be obtained through the "two-step verification" procedure if your devices don't qualify for "two-factor authentication" (see following articles). There's a discussion of app-specific passwords towards the end of the second article.

My own problem (similar to that of hanjive), however, is accessing iCloud email via the genuine Apple email client app built into my Apple iPod Touch. In principle this should not have been affected by the new security regime implemented on June 15th but I gather that some Apple users have encountered problems.

Hope you can manage to figure things out - these new security procedures do seem rather complex! vortex307

Availability of two-factor authentication for Apple ID - Apple Support

Two-step verification for Apple ID - Apple Support

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Answer 9

hanjive Author

Level 1

16 points

Jun 17, 2017 10:15 AM in response to vortex307

You didn't mention if you were using "two-step verification"

Right you are I did not mention that as I had not enabled it - perhaps stubbornly - I was [am] of the mind that the "issue" of not being able to check/send email via Apple Mail program on a Mac running OS X v10.6.8 is related to 2-factor authentication NOT two-step verification. Below is a link to a decent description of the former with a comparison of it with the latter.

Two-step verification for Apple ID - Apple Support

Frankly, after going over that support page, I'm uncertain if implementing that is going to solve the "issues" of accessing iCloud account using the programs Mail and iCal/calendar on device(s) that I choose not to or can't update to OS X El Capitan (or later). I can see how it (two-step verification) will "kick-in" (be invoked) when logging into iCloud via web-browser - not sure how it would work (or can work) using Apple Mail or iCal programs. All of that said I'm gonna go thru the steps via web browser now for one of my iCloud accounts.

I still cannot receive emails to my iPod Touch (get the message that my user name or password is incorrect, but they're not!),

If you mentioned it before I missed it - what version of iOS is the iPTouch running? If it is a version that does not support the new security 2-factor authentication protocol - then setting up two-step verification might resolve the symptoms on our iPTouch.

Anxious to hear back what Apple Support shares with you. If not already - point them to this thread!

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Answer 10

Eric Root

Level 10

685,311 points

Jun 18, 2017 1:27 PM in response to MacLady

There is a contact link.

Apple ID Support

Apple ID Support (2)

Apple Support by e-mail or chat Select your device, Battery, Power and Charging, then Power adapter not working to get a chat option.

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Answer 11

hanjive Author

Level 1

16 points

Jun 18, 2017 6:38 PM in response to 9MacLS

So, after click generate the Password from app-specific passwords, do I just copy and paste the password in the password section of the incoming/outgoing server ?

That is what I did and as of this writing it has resolved the issues in the OP. I did not DELETE the account - rather I simply "updated" the account settings, as appropriate, and pasted the A-SP where it was needed - replacing the one that was previously saved.

3. Should I use the new advised iCloud IMAP server as the previous post suggested (same as shown in my attached picture) or you did it fine with the original server mail.me.com and smtp.me.com ?

Jury (including me) is still out on that one - my "working configuration" for iCloud account on MacPro running OS X v10.6.8 specifies mail.me.com for incoming server - sans imap. Someone else commented in thi thread that they were using the same as you for incoming and they could not retrive email. Would not "hurt" if you removed "imap." and tried to retrieve after the settings were saved - suggest you QUIT and the OPEN the program.

4. As it said "app-specific password", I believe this "generate password" should be used for each apps only and it shouldn't effect to my email in other devices iPhone 6 (10.1.1), iPhone 4s that currently I can receive/send email fine, right?

If I am following your train of thot - Yes the A-SP is only to be used for the program/app & machine you created it for. If you have the same program on a different machine - I am reasonably cofident saying that you need to create another A-SP for that device. THAT SAID - your iPhone 6 & iPhone 4s are probably still working because you already added them to your Trusted Devices associated with you AppleID.

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Answer 12

Jun 19, 2017 2:42 PM in response to conquip

Your Android device is considered a 3rd party. So, you are going to need to sign into the mail app once you have been able to set up Two-Step Verification or Two-Factor Authentication.

Once you have completed the Two-level security setup, you will then be able to generate an App-specific password. You would use this password to sign into your email account instead of your regular Apple ID password.

Using app-specific passwords - Apple Support

Cheers,

GB

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Answer 13

9MacLS

Level 1

21 points

Jun 21, 2017 5:48 AM in response to Winston Churchill

I am not confused and totally understand because I have read everything. As per my posted " I've never turn on any of my devices for Two-Factor Authentication. And I requested the Two-Step Verification and received email confirmed Two-Step Verification which attached the picture above as well, however, I requested Two-Step Verification by clicking on the link Set up two-step verification now. And as per apple information, it listed Two-Factor Authentication is only work on IOS 9 or later or on your Mac with OS X El Captian or later but my mac is 10.6.8, I posted with the picture that mentioned about that or even you go to the link about Two-Factor Authentication it will tell you if your version is older you need to use Two-step verification instead.

The problem I see now which I don't know what's wrong and what other people see in their page but for me, through the page Manage your apple ID it doesn't show where to click turn on/off Two-Factor or generate app-specific password but my iphone6 (10.1.1) automatically have option to turn in on (which I didn't turn in on) and I don't see Two-Step Verification on the page aslo, but when I requested it, I did it through the link set-up now.

I think I will have to contact the Apple Senior Advisor to help, because he works with me by monitor and see my screen in same the time, so whatever I explain he will totally see it by his eyes as well.

Because when this email problem happened I explained to the apple support staff level 1 and he kept rejecting that it's impossible even I told him to go check in this communities that there're many people are having the same problem like me, I can send the link to his email but he refused to check. Again someone may say using 10.6.8 and don't have the problem with mail.app, I would say the same, YES/NO for me, yes I have the problem with @mac.com and no I don't have a problem with the other email, I am not so quite sure but I am just wondered maybe because it's not link with icloud server or using it as APPLE ID. Even I try to recreate my @mac.com account on my husband computer 10.6.8 as well, it's not working as wel.

Since I follow this thread, there are 2 users hanjive and pigmini are able to fix their problem with using app-specific pasword even though it said you only need for the 3rd-party apps which mail.app suppose to working fine without it.

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Answer 14

hanjive Author

Level 1

16 points

Jun 21, 2017 9:14 AM in response to 9MacLS

however, I requested Two-Step Verification by clicking on the link... information, it listed Two-Factor Authentication is only work on IOS 9 or later or on your Mac with OS X El Captian

@9MacLS if after clicking the link you specified...

https://appleid.apple.com/manage/security/2sv/enrollment

... you see "two-step authentication" on your AppleID management page and clicking it loads that information about those minimum requirementsblah blah, look a little further down and I recall there is a statement or two "if you do not have... use two-step verification..." and associated hyperlink to click which as I recall makes you log-in a 2nd time - keep going and just ignore the "label" and click - you will see that two-step verification dialogue in my immediately prior post.

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Answer 15

hanjive Author

Level 1

16 points

Jun 16, 2017 3:39 PM in response to vortex307

Hey vortex307 -

I did receive the email notification on June 12th from iCloud re: app-specific passwords being required to access iCloud data using third-party apps. But, my current problem (and yours) apparently relates to the impact of these changes for existing Apple users.

Exactly!

In its infinite wisdom - I'd like to believe that Apple considered and provided a "back-door" solution that supports folks running versions of OS X sans built-in 2-factor authentication (those prior to El Capitan backwards to at least v10.6.8) so we can continue to interface with Apple's built-in basic/essential productivity software (Mail, iCal, etc)[non-3rd-party programs]. Similar to how some of us have done it since "MobileMe" was replaced by IMAP-only iCloud.

On a computer running OS X v10.7.5 [which does not have "built-in" 2-factor authentication], I just opened up Mail and after entering passwords for incoming and out going servers I was able to send/receive email successfully. In light of that "success", I am going to check/compare the "server" settings between the two different OS X/Mail configurations. Push comes to shove perhaps adding the account back in OS X v10.6.8 might due to trick?

I currently have an outstanding case file open about this, which is being handled by an upper tier supervisor who said she would be in touch with engineering staff.

Anxious to learn what they share with you. TIA.

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