Using Mailkit with Powershell

Question

Using Mailkit with Powershell

David Marino 136

I can run the attached PS script in the PS ISE, but it fails when I run it through a PS window. I can manually execute each command in the PS window without any issues. It looked like the subsequent commands did not "see" the previous commands, and I put in a sleep -s 5 commands after each of the previous commands leading up to the class definition. It did not matter, it failed very quickly. Using the -noexit -Sta parameters did not change the outcome. I ran PS as an Administrator, .\LoadMailkit.ps1 This is for internal use only to send alerts, and therefore I don't need any of the additional functions; attachments / use with gmail, etc. Thank you for your help. ---------- PS 5 Error: At F:\apps\Everbridge\PS\LoadMailKit.ps1:18 char:36 + class MailboxAddressExtended : MailboxAddress { #does not allow p ... PS 7 Error: ParserError: F:\Apps\Everbridge\PS\LoadMailKit.ps1:18 Line | 18 | class MailboxAddressExtended : MailboxAddress { #does not allow p … | ~~~~~~~~~~~~~~ | Unable to find type [MailboxAddress]. [75860-loadmailkit.txt][1] PS 5 Major Minor Build Revision ----- ----- ----- -------- 5 1 18362 1110 PS 7 Major Minor Patch PreReleaseLabel BuildLabel ----- ----- ----- --------------- ---------- 7 1 0 ---------- [1]: /api/attachments/75860-loadmailkit.txt?platform=QnA

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Answer 1

David Marino 136

The attached file provides basic integration of MailKit / Mimekit with Powershell 5. Used only for sending basic text alerts from Powershell, which means it doesn't have any of the other features of MailKit / Mimekit; i.e. Attachments, authentication to external mail services, etc.

76387-simplepsloadmailkitexample.txt

Tested on PS 5
Major Minor Build Revision
----- ----- ----- --------
5 1 18362 1110

Answer 2

Rich Matheisen 48,036

Try dot-sourcing that LoadMailKit.ps1 script instead of just running it (note the two periods, separated by a space):

. .\LoadMailkit.ps1

about_scripts

David Marino 136 Reputation points

2021-03-09T20:37:28.287+00:00
Thank you for the feedback, unfortunately it gave me the same exact error in PS5 / 7:
-PS 5 Err:

At F:\Apps\Everbridge\ps\LoadMailKit.ps1:18 char:36

class MailboxAddressExtended : MailboxAddress { #does not allow p ...

~~~~~~~~~~~~~~
Unable to find type [MailboxAddress].

From the cmd prompt, I have tried

Powershell.exe -noexit -file F:\Apps\Everbridge\ps\LoadMailKit.ps1

Powershell.exe -Sta -file F:\Apps\Everbridge\ps\LoadMailKit.ps1

Powershell.exe -noexit -Sta -file F:\Apps\Everbridge\ps\LoadMailKit.ps1

F:\Apps\Everbridge\ps> . .\LoadMailkit.ps1

At this point I'm not sure if there is some incompatibility with an underlying technology, PS, and Mailkit. Unfortunately the error is not sufficient to point me in the right direction.
/r
Rich Matheisen 48,036 Reputation points

2021-03-09T22:25:46.217+00:00

So where is the class MailboxAddress defined?

The class MailboxAddressExtended inherits from class MailboxAddress.
David Marino 136 Reputation points

2021-03-10T03:01:55.437+00:00

If I'm not mistaken MailboxAddress is defined in the MimeKit DLL, which is loaded first.

The class definition (class MailboxAddressExtended : MailboxAddress....) is dependent on the DLLs being loaded first. I systematically loaded each component through the PS script and the error occurs after the above class definition. There appears to be a disconnect between the previous DLL load commands and the class definition since there are inter-dependent. But the disconnect is only evident when the script is run in the PS window. I don't have a problem in the ISE or if paste the commands into the PS window, one section at a time. I never tried copying everything at once.

It appears like the DLL is not ready to be reference by the time the class is defined. I tried putting a start-sleep -s 2 after loading the DLLs but that didn't help.
David Marino 136 Reputation points

2021-03-10T15:36:20.663+00:00

I decided to take a different tact to the problem.
The solution I was using I found on the Internet, and while it brought me closer to my goal, it was problematic. I needed to add more than one recipient which was the reason for the class definition in the original solution. Instead of defining a class, I decided to port over the InternetAddressList directly from MimeKit, see attached txt file. Reading through the documentation and viewing the original solution, this seemed to be what I needed to meet my needs.

Using my solution I was able to send a basic alert text message on a PS 5 window without any issues.

Thank you for all your help.

76391-simplepsloadmailkitexample.txt
Rich Matheisen 48,036 Reputation points

2021-03-10T15:38:04.847+00:00

Is it possible that the DLL is locked by a previous access in the ISE and that the attempt to use it fails when you try to access it in another process? The ISE (and maybe other IDEs) use the PowerShellToolsProcessHost and that "remembers" things.

Have you tried using LoadWithPartialName (even though it's deprecated)?

Searching for "powershell load DLL" turns up a lot of problems, some of which have usable solutions/work-arounds.
Rich Matheisen 48,036 Reputation points

2021-03-10T15:42:00.367+00:00

Is there a reason why you couldn't use the Send-MailMessage cmdlet for this? I don't know if it's available in .Net core, though.

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Using Mailkit with Powershell

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