IMAP, allow insecure authentication

If it's a Gmail account you might need to set to allow insecure apps in Google Settings.

Allowing less secure apps to access your account - Google Account Help

Found these comments by a user in my notes:

Called Apple Support.

When I called (chatted, really), they had me open KeyChain Access and search for "veri"

I went through each entry and deleted all the ones with a red warning (usually including "unauthorized" or "Unknown").

Then they had me restart and Google accounts started working again, and I could add new ones.

I did have to re-enter all the passwords, but it's not a bad as I feared it would be.

This is what I posted in the bug report:

Title: IMAP Allow secure authentication checkbox doesn't stay selected

Summary:

During setting up an account that needs in the IMAP settings the "Allow insecure authentication" check box to be selected, the checkbox doesn't stay selected after clicking OK. So I cannot connect to the accounts that demand this option.

Other people have the same exact problem: https://discussions.apple.com/thread/8087473?answerId=32572292022#32572292022&ac_cid=tw123456&replyId=32572292

Steps to Reproduce:

Apple mail Account--> Server settings --> IMAP --> Uncheck "Automatically manage connection settings" --> Click "Advanced IMAP settings" --> Check "Allow insecure authentication" --> Click OK. Then click "Advanced IMAP settings" again, the checkbox is unchecked.

Expected Results:

That the checkbox remains checked.

Actual Results:

The checkbox doesn't remain checked. Thus, I cannot connect to my account.

Version/Build:

macOS 10.13.1 (17B48)

Hello and welcome to Apple Support Communities, mauzzz.
If I understand your post correctly, you're having trouble saving your settings for your mail account. I'd like to help.
Safe mode will tell us if the issue is related to a startup item or plugins, and sometimes corrects the issue. This article will tell you how: Use safe mode to isolate issues with your Mac
If everything is working correctly in safe mode, but is not working when you get back to your user account, please check the section titled "If an issue doesn't happen in safe mode" for the next troubleshooting steps.
If the issue continues while in safe mode, a test user will let us know if the issue is isolated to your account, or system wide: How to test an issue in another user account on your Mac. If the issue happens in the test user also, then please check the section titled "If an issue happens in more than one user account."
Let us know if that resolves this issue for you.
Thanks for using the Apple Support Communities. Take care.

Just to be clear, this is a peer to peer support forum. While on occasion, an Apple tech will reply here most replies are from users just like you.

I was assuming you were a single user not from a large group like your institute. Normally, you do not install the newest version of an OS to your users since the first release is generally buggy. Someone should have installed High Sierra to test before having others upgrade.

I have two suggestions until Apple fixes.

1) Use webmail. Since it's IMAP all changes will be reflected when you download.

2) Use Outlook, Spark, Thunderbird, Postbox(has 30 day trial) or other third party app to see if they will connect.

I do not think one can talk about a “particular setup”, which Apple has no idea about. It might not be a setup which is needed by a mojority of users. However it is some kind of a standard. I do not understand the debate. I do not understand the Apple Care guy, whith who is constantly trying to blame anyone else rather than the mail app. Why should Apple implement a button/menu “advanced IMAP setting” in the mail App if 1) no one needs it, or, 2) Apple does not want ppl to have the option to choose it, or, even 3) Apple wants to force ppl not to use it, or, hypothetically if 4) the setting is for professionals only and Apple mail is for amateurs. Anyway let’s continue. Clicking this button opens a window. In this window there is this checkbox we are all talking about. Why should Apple implement a checkbox “allow insecure authentication” if 1) no one needs it, or, 2) Apple does not want ppl to have the option to choose it, or, even 3) Apple wants to force ppl not to use it, or, hypothetically if 4) the setting is for professionals only and Apple mail is for amateurs. Apple obviously wants user to be able to choose this setting. Now coming to the checkbox. You can click it. Then it is “selected”, or let’s say activated. When u close the window and reopen it, the checkbox is unmarked/unchecked/unselected, i.e. the setting is inactivated. This means the setting cannot be stored. That is the problem we r talking about. Now 1) it is a bug, or 2) Apple programmed it itentionally, that the checkbox can not be activated permanently, or 3) there is indeed a condition which forces the option to be automatically deactivated. Guess option 2) is unlekly, Apple could have simply omitted all the options. Again, why should it implemented in the app, if Apple does not want the user to have this option to choose. 3) everyone who encountered this problem reported everything worked fine under Sierra, with the same settings. And the checkbox remains activated in Sierra! Third party applications are working fine on high Sierra with the same server settings and option of “insecure transmitted Password” for authentication. Unimaginable that all of us meet a mystical criterion in the setting which forces the option to be automatically deselected. The provider’s problem? I do not think that there is any datatransfer beween app and provider at the stage of clicking the checkbox. And even if it is the case, I am sure, it would have been programmed differently, by -for example- warning messgae or similar. Therefore, 3) is unlekly too. Or Apple should explain why and in which circumstance the checkbox is deactivated automatically. 1) Common guys, there is plenty of evidence(?), that this rproblem is a “bug”, right? I am tired of this, honestly.

By the way there was a security update for Sierra. Problem remains unsolved, as already indicated.

Have you tried removing the app in Mail? This takes you to System Preferences > Internet Accounts.

Don't just uncheck Mail, remove the account and add it back

I have exactly the same issue. It's a bug. It also present in the betas of High Sierra. I cannot use my main work email account without that option checked, so I am using an alternative email client for the time being. I am just waiting for 10.13.1. Hopefully, it will be fixed there.

The article deals with accounts that use SSL/TSL (and security certificates). The issue mauzz mentioned is about accounts that use insecure IMAP authentications, no certificates involved. So the article does not apply to this issue.

It's not a settings/setup issue. It is a bug.

Yes ! That is same case I use . I use Davmail to transfer my mail from exchange server to my Mac . But mail.app IMAP setting does not allow the insecure connection to my localhost. By the way, SMTP setting accept the insecure connection. This is big BUG but not be repaired even in the beta 4.

I feedback this to Apple support in China. After about an hour chat, they confirmed the bug in their Mac but have no solution.

Sorry for my poor English.

Update: another phone call with the apple care guy. Engineers team gave him instructions to perform come commands in the terminal.

first: open date and time preferences and select "show seconds" type in terminal "ls -aOle@R ~/Library/Mail"

and then export output

then: open mail, reproduce problem, take a screenshot showing that the checkbox is unselected when you reopen the window advanced IMAP setting, (my opinion, a screen recording (video) would have been better), type in terminal "sudo sysdiagnose -X Mail", export

the guy will forward it to the engineers team

he will call back once he receives a feedback, great!

Still not fixed. I've got a Macbook running Sierra and this works fine (ditto for a Mac Pro running Snow Leopard). I've got a Macbook and an iMac running High Sierra, fresh installs. Both have this same issue where the setting for "Allow insecure authentication" will not stay checked. I'm trying to IMAP to a server on my local network--trivial thing, at least it used to be.

Anyone know of a way to communicate to Apple about a bug to push for it to get fixed?

BugReporter http://bugreporter.apple.com

Free ADC (Apple Developer Connection) account needed for BugReporter. Setup a free account

http://developer.apple.com/programs/register/

How to attach a sysdiagnose to send Bug Report

Mac OS X Feedback (no account needed)

https://www.apple.com/feedback/macos.html

Use Outlook, Spark, Thunderbird, Postbox(has 30 day trial) or other third party app to see if they will connect.

You can follow the guidance of dianeoforegon the best method if any issue are in the mail delete the account and add it Set up Mail with email accounts - Apple Support

Use SSL to connect to an SMTP email server - Apple Support

It does affect others. As I said, it is my work account that requires this setting to be checked. Everyone in my workplace that is using Mail.app in 10.13 is having the same problem with their work email. It is a national research institute with hundreds of informatics researchers. My boss downgraded back to Sierra because of this specific bug. It is a systemic problem in Mail.app in 10.13. It is not a configuration issue. It's ok, all software has bugs, including Apple's. But refusing to acknowledge it and blaming mauzz's configuration hinders the fixing of the bug and the improvement of the quality of Mail.app