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You have configured WinSCP to wait for 90 seconds. The default timeout is 15. Still, I admit, this should be done in a separate thread and we plan to improve this.
Stephen Lujan

with apologies for the delay...

Re: application freezes while attempting to sync a fifo file

Please attach a full log file showing the problem (using the latest version of WinSCP).

To generate log file, enable logging, log in to your server and do the operation and only the operation that causes the error. Submit the log with your post as an attachment. Note that passwords and passphrases not stored in the log. You may want to remove other data you consider sensitive though, such as host names, IP addresses, account names or file names (unless they are relevant to the problem). If you do not want to post the log publicly, you can mark the attachment as private.
Stephen Lujan

application freezes while attempting to sync a fifo file

There may likely be a network issue at play and it would be easy to believe Solaris is instigating a problem. I believe its just a problem with a network operation blocking the main thread in WinSCP. WinSCP seems to stall and is reported as "not responding" by windows. It becomes impossible to hit the cancel button or even close the application without just forcefully killing the process from task manager. If you wait 90 seconds the application unlocks with an error message.

The way I've reproduced this:

1 make a new folder on Solaris
2 create a fifo file using "mknod ./test p" in your new folder on Solaris
3 create a new folder in windows
4 open each folder in WinSCP 5.5.5 running under windows 7
5 click the synchronize button
6 switch to local and leave the other settings at default and hit ok
7 the synchronization checklist will just have the fifo file copying to windows so hit ok

The "synchronization" window pops up, but The main window and the synchronization are immediately rendered unresponsive. With the time elapsed never getting past 0:00:00. I either kill it or wait until 90 seconds pass and the "Host is not communicating for more than 90 seconds" error pops up.

I don't know if the network error is caused by WinSCP or the host, but any operation that can take 90 seconds should be done in a separate thread so the main thread can keep pumping windows events and cancel the operation if the user chooses. The fifo files also break any multi file synchronization in progress. Because of this, I have to manually deselect a bunch every fifo file when synchronizing my folders.