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Old 28 Dec 2021, 04:25 PM   #31
BritTim
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Quote:
Originally Posted by camner View Post
Followup...

<snip>

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
Thanks for the feedback. If you have the skills, time and motivation, I would be extremely interested in what Wireshark could reveal about this problem from the client end. It might even provide clues enabling you to circumvent the issue.
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Old 28 Dec 2021, 04:32 PM   #32
BritTim
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One thing I forgot to suggest earlier that, at least, changes the way Fastmail is contacted by the client, is to use Fastmail's proxy servers. Take a look at https://www.fastmail.help/hc/en-us/a...ames-and-ports in the section Firewall Access. It probably will not make any difference, but it might.
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Old 29 Dec 2021, 03:38 AM   #33
camner
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@BritTim: Thanks for the tip about WireShark. I may take a look, and if it seems doable for me, might give it q whirl.
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Old 29 Dec 2021, 05:22 AM   #34
hadaso
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I would think that if Outlook doesn't contact Fastmail's server then it's an issue to be handled by Microsoft's support and not Fastmail's support...
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Old 29 Dec 2021, 09:43 AM   #35
n5bb
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I have several Fastmail accounts. I just added two of them to my local Outlook email client on Windows 11, and the setup went smoothly and tests worked well. I suggest:
  • Be sure you are using the latest version of the Outlook email client. Mine says: "Version 2111 Build 16.0.14701.20254) 64-bit". .
  • If you are only using Outlook for Fastmail, remove Outlook and re-install a fresh copy. If you don't want to do that, remove any old Fastmail attempted account setups and reboot your PC.
  • When adding the Fastmail account, let Outlook do the server setup automatically (IMAP and SMTP ports, etc.). All you need to enter is your Fastmail account main email address (you can't use an alias) and an Application Password. Let Outlook save the password. When you generate and use that Application Password, there is no need for you to save it anywhere else, so it will only be saved inside your Outlook app (securely).
  • Always use a unique Fastmail-generated Application Password for each email client which will be accessing your Fastmail account. This makes troubleshooting and cleaning up if there is a security breach (such as a stolen laptop) much easier.
  • The Outlook client will automatically send a test message to your Fastmail account. The message will be sent by the Outlook client using the Fastmail SMTP and it will be addressed to your Fastmail email account. The subject is "Microsoft Outlook Test Message".
Bill
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Old 29 Dec 2021, 01:07 PM   #36
camner
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Quote:
Originally Posted by hadaso View Post
I would think that if Outlook doesn't contact Fastmail's server then it's an issue to be handled by Microsoft's support and not Fastmail's support...
Well, I didn’t know that Outlook not contacting FM’s servers was a possibility until I reached out to FM support and they told me (after all, all Outlook told me, “helpfully,” was that “Something went wrong”)! . [I don’t think FM support told me that was true specifically in my case but rather was making a more general statement about what they have found]
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Old 29 Dec 2021, 01:08 PM   #37
camner
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Quote:
Originally Posted by n5bb View Post
I have several Fastmail accounts. I just added two of them to my local Outlook email client on Windows 11, and the setup went smoothly and tests worked well. I suggest:
  • Be sure you are using the latest version of the Outlook email client. Mine says: "Version 2111 Build 16.0.14701.20254) 64-bit". .
  • If you are only using Outlook for Fastmail, remove Outlook and re-install a fresh copy. If you don't want to do that, remove any old Fastmail attempted account setups and reboot your PC.
  • When adding the Fastmail account, let Outlook do the server setup automatically (IMAP and SMTP ports, etc.). All you need to enter is your Fastmail account main email address (you can't use an alias) and an Application Password. Let Outlook save the password. When you generate and use that Application Password, there is no need for you to save it anywhere else, so it will only be saved inside your Outlook app (securely).
  • Always use a unique Fastmail-generated Application Password for each email client which will be accessing your Fastmail account. This makes troubleshooting and cleaning up if there is a security breach (such as a stolen laptop) much easier.
  • The Outlook client will automatically send a test message to your Fastmail account. The message will be sent by the Outlook client using the Fastmail SMTP and it will be addressed to your Fastmail email account. The subject is "Microsoft Outlook Test Message".
Bill
Thanks for your suggestions. I will give them a try.
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Old 29 Dec 2021, 01:53 PM   #38
n5bb
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Quote:
Originally Posted by camner View Post
Thanks for your suggestions. I will give them a try.
Also, don't forget about this Microsoft tool (which can perform some repairs on Outlook):
Microsoft Support and Recovery Assistant

According to that website, the Microsoft Support and Recovery Assistant offers the best solution for these identified problems:
  • Outlook won't start
  • I can't setup my Microsoft 365 email in Outlook
  • Outlook keeps asking for my password
  • Outlook keeps saying "Trying to connect..." or "Disconnected"
  • Shared mailboxes or shared calendars don't work
  • I'm having problems with my calendar
  • Outlook stops responding
  • Outlook keeps crashing
  • I can't send, receive, or find email
I have not used this tool on Outlook myself, since I haven't experienced any of those problems.

Bill
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Old 29 Dec 2021, 10:15 PM   #39
BritTim
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Quote:
Originally Posted by n5bb View Post
Also, don't forget about this Microsoft tool (which can perform some repairs on Outlook):
Microsoft Support and Recovery Assistant

According to that website, the Microsoft Support and Recovery Assistant offers the best solution for these identified problems:
  • Outlook won't start
  • I can't setup my Microsoft 365 email in Outlook
  • Outlook keeps asking for my password
  • Outlook keeps saying "Trying to connect..." or "Disconnected"
  • Shared mailboxes or shared calendars don't work
  • I'm having problems with my calendar
  • Outlook stops responding
  • Outlook keeps crashing
  • I can't send, receive, or find email
I have not used this tool on Outlook myself, since I haven't experienced any of those problems.

Bill
I have used older versions of that tool. Like the Windows tool you can use to try to solve problems with devices (such as sound) I have found it rarely does anything useful. Worth trying, of course.
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Old 30 Dec 2021, 09:56 AM   #40
Terry
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Are you trying to use an alias and not you main F/m acc....just a thought
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Old 30 Dec 2021, 12:30 PM   #41
BritTim
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Originally Posted by Terry View Post
Are you trying to use an alias and not you main F/m acc....just a thought
Any suggestions we make must acknowledge the most important clue: the same user and password works with Thunderbird. Also important is that Fastmail claims that their servers do not see the connection attempt. This points to something quite strange, not just finger trouble by the person trying to set things up.
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Old 31 Dec 2021, 10:27 AM   #42
camner
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I have tried the various suggestions you helpful folk have made.
  1. I completely uninstalled Office 365 and reinstalled
  2. I created a new app-specific password
  3. I verified through FM Settings that I was using my "original" FM email (xxxx@fastmail.fm)
  4. I tried using the FM proxy servers with various combinations of ports

....all to no avail.

I am running Outlook version 2111 (Build 14701.20262 Click to Run)

At this point, I think I have to give up. I have no idea why my PC won't allow Outlook to connect to FM, but at this point I have no idea where else to turn to try some new trick.

I want to express my gratitude to so many of you who volunteered your time to try to help me out; I truly appreciate it. It's why I have stayed connected to this community for so many years.
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Old 31 Dec 2021, 10:32 AM   #43
somdcomputerguy
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Quote:
Originally Posted by camner View Post
At this point, I think I have to give up. I have no idea why my PC won't allow Outlook to connect to FM, but at this point I have no idea where else to turn to try some new trick.
I'm not sure if this has been mentioned or not. Do you have any kind of AntiVirus program or other type of firewall in place?

- Bruce
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Old 31 Dec 2021, 10:34 AM   #44
camner
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Originally Posted by somdcomputerguy View Post
I'm not sure if this has been mentioned or not. Do you have any kind of AntiVirus program or other type of firewall in place?

- Bruce
Nope (other than Windows Defender)
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Old 31 Dec 2021, 10:39 AM   #45
somdcomputerguy
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Originally Posted by camner View Post
Nope (other than Windows Defender)
Even that may be enough. Microsoft products may be especially Defendable. Try disabling it or having it not run after a reboot. I understand how frustrating this can be, believe me. Try again, hopefully this will be successful.

- Bruce
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