I updated Win10 on Friday. cmd.exe starts:

Microsoft Windows [Version 10.0.19045.3636]
(c) Microsoft Corporation. All rights reserved.

C:\Users\ken>
[download]

Your PowerShell commands:

Windows PowerShell
Copyright (C) Microsoft Corporation. All rights reserved.

Try the new cross-platform PowerShell https://aka.ms/pscore6

PS C:\Users\ken> $joiner = [char]::ConvertFromUtf32(0x200D)
PS C:\Users\ken> $pc     = [char]::ConvertFromUtf32(0x1F4BB)
PS C:\Users\ken> $man    = [char]::ConvertFromUtf32(0x1F468)
PS C:\Users\ken> $person = [char]::ConvertFromUtf32(0x1F9D1)
[download]

PS C:\Users\ken> "$man"
👨
PS C:\Users\ken> "$person"
🧑
PS C:\Users\ken> "$person$joiner$pc"
🧑‍💻
PS C:\Users\ken> "$man$joiner$pc"
👨‍💻
PS C:\Users\ken>

Except in the PowerShell window, all of those glyphs just appear as a square with a question mark inside. So, it would appear that the character information is kept: not rendered in the CLI but is rendered in the browser.

I also updated Cygwin on Friday.

$ uname -a
CYGWIN_NT-10.0-19045 titan 3.4.9-1.x86_64 2023-09-06 11:19 UTC x86_64 
+Cygwin
[download]

Your bash commands:

$ echo -e '\U1F468'
👨

$ echo -e '\U1F9D1'
🧑

$ echo -e '\U1F468\U200D\U1F4BB'
👨‍💻

$ echo -e '\U1F9D1\U200D\U1F4BB'
🧑‍💻

Except in the CLI (/usr/bin/mintty) all glyphs just appeared in their text forms. Also, the ZWJ sequence above, appeared as two separate glyphs: MAN + PC.