IMAP, allow insecure authentication

All other applications connect fine (in fact I am using MailMate right now). Only outlook does not connect as it doesn't allow for fine-tuned settings like the ones needed.

sorry, some typos, and uodate for high sierra, not sierra....

all right folks, that's it! guess there is nothing more which can be done,

waiting for an OS update...

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Apple released macOS High Sierra 10.13.3 today, Does anybody confirm whether apple fixed this bug ? I downgrade to Sierra last week because can not wait anymore ...

no, it's not fixed.

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?

Most commercial/consumer providers offer secure settings. As I said, it is my work email. It is a large national informatics research institute. Just because they use "insecure authentication" doesn't mean that it is insecure. They use much stricter ways, to ensure the security (SSH key-based machine authentication and SSH tunneling).

Same issue.

Tried

1.) create and use new admin account

2.) root account

3.) reboot safe mode

4.) reinstall OS (high sierra)

5.) erease HD, reinstall

6.) chatted and then called Apple (Europe based...), explained, told them I am not the only one on planet, told them probably works fine with Sierra, as on two other older macs I did not have this issue. However as I had no access to them, I was told to check whether they run on Sierra for sure and call back. Had the feeling he understood it’s an Apple Mail problem (essentially a bug), but did not acknowledge it... saying „hmmmm“ „hmmm“ „you have to check wether the other macs eun on Sierra, in order to narrow the problem down...“

7.) later, checked on one older mac, indeed Sierra, works fine

8.) checkt other old mac, Sierra, upgraded to High Sierra, problem appeared, downgraded it using time machine, worked again

9.) installed thunderbird on high sierra, works fine

10.) Common! It‘s a bug!

Did not have time to call them back, will do a.s.a.p.

however I have to work and I can‘t deal with this the whole day (and night), and I need my E-mail for my work.... 😫🙄 frustrating

All right, had another 2 calls with the same apple care guy.

The first call: He told me I should check with other E-mail accounts, what happens if I click the checkboxes. As I was on the way, I could not check it right away. So I went home, checked with 3 different Mail accounts what happens. Surprise surprise, same effect.

Meanwhile, a tech from the mail provider called, yes it was already the case with beta version, and they informed Apple. And I asked specifically, is this an Apple mail problem? Yes, almost certain.

Second call: The Apple guy asked what the results were. I told him same effect. He told me, that the engineering department could not reproduce it. As an example, it works in case of Gmail. Gmail? Really? The guy said, he just tried it by himself. I asked him how he managed to do so. After a screen-sharing session, surprise, surprise, he was talking about the SMTP setting. Oh well that, I (we) knew already a long time ago, that the checkbox remains marked for SMTP insecure authentication... Common, are these guys serious? I really started to feel some kind of anger, and I raised my voice and told him, that we were talking about IMAP settings. After almost an argument, he finally admitted that this was kind of a mistake he made. But, in some cases, the engineering department allegedly said, it is to be expected or normal, as an example "hotmail"(really?), and "apple" (not iCloud, the corporate mail). What does it mean "normal"? Some kind of a wishy-washy response. But basically the suggested it is (likely?) not a problem of Apple mail / HighSierra, it is the provider. Then I have to discuss with the provider. Oh yeah, so it is really the problem of the provider that the checkbox cannot be marked permanently? And what about the postings in the official apple support communities (this site)? Ah you know, there might be millions of different reasons, and you know people are only posting if things are not working, and not if things are working, kind of... oh ok, so the idea is everybody should post that mail app is working for Gmail-acoumts? (I really lost patience and got energetic) R u really sure it's not a bug? Can you prove it? Explain it? And then, yea maybe, maybe not... he will again contact the engineering department and get back to me in four days. Great!

Hey guys, in particular "mauzzz", "polokov" and "yunsmet", any inputs, any news? What shall tell this guy when he calls back? Good arguments, to explain it is a bug!?

@yunsmet, did Apple support China indeed said "it is a bug" essentially admitted "it is a problem of mail app on HighSierra"?