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MSN for Mac client testing #2

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opened 2026-06-16 00:51:27 -05:00 by CursedSilicon · 2 comments
CursedSilicon commented 2026-06-16 00:51:27 -05:00
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Hi team,

Bredo and myself set up an Azul server for MSN internally on CGHMN

I downloaded some of the old Mac MSN clients from Macintosh Garden for testing. These are "official" Microsoft clients rather than 3rd party ones such as Adium or Pidgin.

We were able to verify HTTPS MSN services are working after generating and adding the CGHMN CA on the network to the required client(s). Windows MSN Messenger 6.2 and Mac MSN Messenger 3.0.0 were successfully able to communicate via text (but not share files. Unsure if this is also related?)

All other versions tested (4.0.1, 7.0.3 and 8.0.0) fail to connect.

I've attached Wireshark logs for each failed version. Unfortunately the git server required me to rename them to txt in order to attach them. Rename them back to pcapng and they should open in Wireshark as normal.

All testing was done on a Mac Pro 5,1 (early 2010) with Snow Leopard x86 (10.6.8).

All clients before 8.0.0 run under "Rosetta" PowerPC emulation. If desired, further testing can also be done on a PowerPC Mac running Leopard (10.5.8)

https://macintoshgarden.org/apps/msn-messenger-mac-version-30
https://macintoshgarden.org/apps/msn-messenger-mac-401
https://macintoshgarden.org/apps/msn-messenger-mac-702
https://macintoshgarden.org/apps/msn-messenger-mac-800

Hi team, Bredo and myself set up an Azul server for MSN internally on [CGHMN](https://www.youtube.com/watch?v=cSJsGNIDjtc) I downloaded some of the old Mac MSN clients from Macintosh Garden for testing. These are "official" Microsoft clients rather than 3rd party ones such as Adium or Pidgin. We were able to verify HTTPS MSN services are working after generating and adding the CGHMN CA on the network to the required client(s). Windows MSN Messenger 6.2 and Mac MSN Messenger 3.0.0 were successfully able to communicate via text (but not share files. Unsure if this is also related?) All other versions tested (4.0.1, 7.0.3 and 8.0.0) fail to connect. I've attached Wireshark logs for each failed version. Unfortunately the git server required me to rename them to `txt` in order to attach them. Rename them back to `pcapng` and they should open in Wireshark as normal. All testing was done on a Mac Pro 5,1 (early 2010) with Snow Leopard x86 (10.6.8). All clients before 8.0.0 run under "Rosetta" PowerPC emulation. If desired, further testing can also be done on a PowerPC Mac running Leopard (10.5.8) https://macintoshgarden.org/apps/msn-messenger-mac-version-30 https://macintoshgarden.org/apps/msn-messenger-mac-401 https://macintoshgarden.org/apps/msn-messenger-mac-702 https://macintoshgarden.org/apps/msn-messenger-mac-800
MSN Messenger MAC 7.0.3.txt
6.1 KiB
MSN Messenger MAC 4.0.1.txt
4.7 KiB
MSN Messenger MAC 8.0.0.txt
2.2 KiB
CursedSilicon commented 2026-06-16 01:16:10 -05:00
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Tangentially related follow-up

Confirmed that file transfers from Windows clients succeed. Sent a file from a 4.7 client to a remote 6.2

image

Tangentially related follow-up Confirmed that file transfers from *Windows* clients succeed. Sent a file from a 4.7 client to a remote 6.2 ![image](/attachments/a16a285b-ff4f-429b-8f96-05fd69c64a52)
image.png
607 KiB
CursedSilicon commented 2026-06-16 01:19:14 -05:00
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Confirmed 7.0 to 6.2 file transfers also work. File transfer failures seem to just be a Mac issue?

image

Confirmed 7.0 to 6.2 file transfers also work. File transfer failures seem to just be a Mac issue? ![image](/attachments/95c2b59e-7738-405a-83f1-5c664f36d7f4)
image.png
130 KiB
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