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Old 16 Dec 2021, 03:36 PM   #16
camner
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I now realize that with my version of Outlook, the steps aren't quite the same as given by @gardenweed.

After Step 10 (choosing IMAP), I do NOT get taken to a screen where I can enter server settings. After choosing IMAP, the next screen for me asks for my password. I enter the app-specific password, and then Outlook whirs away for a while, eventually presenting me with the error message "There was a problem setting up your account." At THAT point, one of the options is "Change Account Settings." Clicking that takes me to a screen that already has the imap and smtp server settings prepopulated (correctly).

There is also NO box to tick for "Outgoing server needs authentication."

FWIW, the version I'm running is: Microsoft® Outlook® for Microsoft 365 MSO (Version 2111 Build 16.0.14701.20206) 64-bit
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Old 16 Dec 2021, 03:40 PM   #17
somdcomputerguy
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Make sure that SPA or Secure Password Authentication is not enabled or selected.

- Bruce
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Old 16 Dec 2021, 05:01 PM   #18
Terry
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Camner have you selected the correct box in the password section in Fastmail as there are quite a few options. If you select the wrong one it wont work.
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Old 16 Dec 2021, 07:09 PM   #19
gardenweed
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Quote:
Originally Posted by camner View Post

FWIW, the version I'm running is: Microsoft® Outlook® for Microsoft 365 MSO (Version 2111 Build 16.0.14701.20206) 64-bit
Mine is part of Office 365 subscription

Microsoft® Outlook® for Microsoft 365 MSO (Version 2111 Build 16.0.14701.20240) 64-bit
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Old 22 Dec 2021, 08:34 AM   #20
Terry
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Did you get it sorted ?
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Old 22 Dec 2021, 12:02 PM   #21
camner
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Originally Posted by Terry View Post
Camner have you selected the correct box in the password section in Fastmail as there are quite a few options. If you select the wrong one it wont work.
I am not certain what do you mean by the correct box option in the password section in fastmail.
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Old 22 Dec 2021, 05:33 PM   #22
BritTim
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Your tests showing that Thunderbird works and Outlook 365 does not (presumably with the same user and password) suggests that Outlook 365 is interacting with Fastmail differently from Thunderbird. While I had problems with Outlook's support for IMAP in the past, this is a bit of a head scratcher. The only thing (password related) that I would caution you on is to be very careful with copy and paste. Apart from unexpected leading or trailing blanks, I have known copy and paste to drop some special characters or otherwise mangle such strings. Try, very carefully, typing the password in.
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Old 22 Dec 2021, 10:44 PM   #23
JeremyNicoll
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Originally Posted by BritTim View Post
The only thing (password related) that I would caution you on is to be very careful with copy and paste. Apart from unexpected leading or trailing blanks, I have known copy and paste to drop some special characters or otherwise mangle such strings. Try, very carefully, typing the password in.
Sometimes if I want to be certain that a value I'm going to c&p somewhere has no extraneous characters in it I'll first type something like

>><<

into a "command line" field, in a text editor I use a lot. The text editor does not allow anything that's got more than one line to be pasted into that field.

Then I copy the value concerned from wherever, and rather than pasteing it into the required application, I try to paste it between the >> and <<. If it works then I know there was no CR or LF involved in the value, and if what I then see has no apparent whitespace between the >> and the visible pasted-in chars, and the <<, I know there were no leading or trailing blanks.
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Old 23 Dec 2021, 06:11 AM   #24
camner
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Originally Posted by BritTim View Post
Your tests showing that Thunderbird works and Outlook 365 does not (presumably with the same user and password) suggests that Outlook 365 is interacting with Fastmail differently from Thunderbird. While I had problems with Outlook's support for IMAP in the past, this is a bit of a head scratcher. The only thing (password related) that I would caution you on is to be very careful with copy and paste. Apart from unexpected leading or trailing blanks, I have known copy and paste to drop some special characters or otherwise mangle such strings. Try, very carefully, typing the password in.
I wish I could say that I only cut and paste the password (because then I could try typing it in myself as a troubleshooting step!), but after failing several times with cut and paste, I tried typing it manually (twice IIRC), failing both times.
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Old 23 Dec 2021, 07:23 AM   #25
Terry
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Originally Posted by camner View Post
I am not certain what do you mean by the correct box option in the password section in fastmail.
The place where you select the APP password.

I have occasionally selected the wrong section and nothing will work.

Perhaps just try mail with all 3 together POP etc

Last edited by Terry : 23 Dec 2021 at 07:28 AM.
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Old 23 Dec 2021, 10:11 AM   #26
camner
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Quote:
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The place where you select the APP password.

I have occasionally selected the wrong section and nothing will work.

Perhaps just try mail with all 3 together POP etc
since the app password I created in fastmail worked with Thunderbird, I think I managed to create a valid app password.

but, I have not yet tried it with varying options for what to allow In terms of mail, contacts, and calendar (and combinations there of). I’ll try varying that and see if I have any better success. Thanks for the suggestion.
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Old 23 Dec 2021, 12:17 PM   #27
Terry
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I’ll try varying that and see if I have any better success. Thanks for the suggestion.
That's what I do sometimes, depending on what I am using
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Old 24 Dec 2021, 05:24 AM   #28
pjroutledge
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Quote:
Originally Posted by camner View Post
since the app password I created in fastmail worked with Thunderbird, I think I managed to create a valid app password.
Have you been trying to use the same app password in more than one app? Fastmail help says "Every third-party program or app needs its own app password to access your information" and "If want to use your Fastmail account with any non-Fastmail service such as your mail client or desktop calendar, then you will need to create an app password specific to that service" (my emphasis)
I take this to mean that different app passwords are needed for different clients.
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Old 24 Dec 2021, 03:36 PM   #29
BritTim
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Quote:
Originally Posted by pjroutledge View Post
Have you been trying to use the same app password in more than one app? Fastmail help says "Every third-party program or app needs its own app password to access your information" and "If want to use your Fastmail account with any non-Fastmail service such as your mail client or desktop calendar, then you will need to create an app password specific to that service" (my emphasis)
I take this to mean that different app passwords are needed for different clients.
I remember this being explained in the past as a security best practice, not something that is enforced. As far as I am aware, this is still true.
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Old 28 Dec 2021, 03:28 PM   #30
camner
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Followup...

I opened a support ticket with FM, and received a not very helpful reply from the 1st level tech. I asked to escalate the ticket, and was told there would be about a week's delay.

Sure enough, a week later I received the following VERY helpful reply from a more senior tech:

Hi,

Thank you for reaching out and am sorry for the trouble you have been facing with your fastmail account setup on Outlook.

I am afraid, this is a known issue with Outlook. We have seen that, in some instances, Outlook simply fails to connect to our servers and throws a generic "Something went wrong" error without any specific reason. As you have noted your machine has no issues connecting to our servers and you are able to setup other email clients fine. Which means this is specifically something internal to Outlook. Annoyingly it only happens in some instances. We have 1000s of Outlook users that do not see this type of error.

Unfortunately since the connection attempts are not reaching our servers we don't really know what exactly is causing this. A few users that reported this problem later mentioned that things started to work after a while without any action from their end.

If you haven't already done so, one thing that might, if this is some Outlook caching issue, is uninstalling Outlook, rebooting your machine and then re-installing it again. Also, if you have any 3rd party security software that might interfere with Outlook setup, I suggest disabling that temporarily until the setup is done. Hopefully one of those works for you.

If not, the only other option is to use an alternate 3rd party app. In general, we highly recommend sticking to our web UI for the best experience. It's much better and reliable than any other email app out there. It supports push notifications as well so you get notified of new emails on browsers that supports notifications (eg: Firefox, Chrome or Safari). Keeping the UI open in a browser makes it behave similar to an email app. But if you must use a 3rd party app, Thunderbird would be a better alternate.

Please let me know if you have any other questions.

Please
Yassar Ali
Senior Support Agent, Fastmail


I am posting the email reply I received for two reasons:
1. To demonstrate the good support I received from FM
2. To help others who might run into the same issue
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