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MSN - Can't trigger IM popup dialog in MSN

I found a problem with MSN where if I send an IM then nothing happens on the receiving side. But if the receiver opens the dialog first, then jabber sends stuff, then it works.

Doesn’t work:

Jabber-MSN user logs in and shows up.

No conversation or IM dialog opened.

Jabber sends IM to MSN user.

Nothing happens.

Works:

Jabber-MSN user logs in and shows up.

Receiver opens dialog to talk to Jabber-MSN and messages Jabber-MSN.

Jabber sends IM to MSN user.

Receiver can see message.

Other notes:

Jabber-MSN logs in fine and I can see the active user.

I tried this on 2 different clients but on the same OpenFire server and IM Gateway.

The receiver was using the Mac MSN messenger client, latest version.

Thank you,

Ryan