IMAP, allow insecure authentication

I'm having a problem with Mail.app in High Sierra. In the advanced IMAP settings I need to set 'allow insecure authentication' but the setting is not saved. Because of this I can not make an IMAP connection. Is this a bug?

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MacBook Air, macOS High Sierra (10.13)

Posted on Sep 27, 2017 3:22 AM

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Posted on Oct 25, 2017 7:12 PM

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.

56 replies

Nov 12, 2017 3:06 AM in response to Neurosurgeon

Allright, called them back, explained all agin. The guy on the phone checked what happens on his Mac in case he clicks the checkbox. Surprise, surprise same effect! "might be a bug, but, he never heard about this issue", But even then, he asked whether I can contact the mail-provider, maybe the mail settings have recently changed.... OK contacted mail provider (same country in Europe): "Thank you for your efforts, the problem is known, we are working with Apple to find a solution". Oh, ok, so obviously apple (in this region) should be aware, but the support guy I talked to was not aware. According to "yunsmet" Apple China should be aware too. Wondering, r they not sharing infos about important issues? Never mind, the guy said he will now contact/forward this issue to the engineering department. But it will take 5 working days until a response can be expected. Great! Let's see what they are saying.

Nov 30, 2017 12:00 AM in response to polokov

Apple sent me following after I filed a bug report:

"Engineering has determined that your bug report (35596588) is a duplicate of 35571476 and will be closed."

have no idea what 35571476 is as I have no access.

Anyway, how do you know that acknowledged in the bug reporting system that it is a bug and on the list to be fixed.

If it is the case, good news.

The apple care guy by phone told me after a week, that he did not receive a feedback from the engineering team.

Oct 26, 2017 11:29 AM in response to mauzzz

mauzzz wrote:


I can't imagine this effects only a few users. Did you send feedback?

The person you are asking if they sent feedback is using a beta version of software. They nor we can discuss beta software here. If you are using beta software please read the NDA you agreed to and report the issue to the beta group.


If you are not using beta software your issue is specific to you and your system configuration. It does not affect others as it is not a systemic problem. Tell us more specifics about your Mail configuration.

Oct 28, 2017 3:10 AM in response to dianeoforegon

Single user or a large group is irrelevant, Anyway, as we are an informatics institute, lots of us need to use the latest Xcode tools and compilers. So we cannot wait because of a bug in Mail.app. We are not a company where the main function of a computer is Microsoft Office.


And as I mentioned before, I am using for now an alternate email client (and yes, I can connect fine).


But I am used to and my workflow is centered around Mail.app, so it is quite annoying.


Let's hope the bug will be fixed in 10.13.1

Nov 29, 2017 10:08 PM in response to dianeoforegon

I think that what you are saying is not possible at all.


1) Despite the "allow insecure authentication" name, the method is much more secure that regular secure authentication. That's because the "insecure" connection is between mail.app and the same computer that the mail.app is running on. From there, it is through an ssh tunnel (think of it as a VPN). That is orders of magnitude more secure as a malicious third party must have access to the ssh private keys to stage an attack.


2) The feature works fine on the mail.app on iOS 11.


3) Appla has acknowledged in the bug reporting system that it is a bug and on the list to be fixed. I assume that they are too busy plugging security holes this period so that bug is not very high on their list right now.

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IMAP, allow insecure authentication

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