I am running cygwin virtualbox running a WinDev2206Eval "appliance" (.ova from microsoft). Everything else I've tested so far in cygwin runs as expected except scp when the file path is an absolute path, e.g. /tmp/foo. Scp references to that file using a relative path, e.g. ../../tmp/foo, work fine. For example: $ ls > /tmp/foo # create a /tmp/file $ ls -l /tmp/foo $ scp /tmp/foo bcserver:foobar # fails with /tmp/foo "file not found" $ pwd # (CWD is /Users/dmk) $ scp ../../tmp/foo bcserver:foobar # this works $ cd /tmp $ scp foo bcserver:foobar # this also works Please see the attached (script) log file scp.log for the actual results using these commands. See also the attached cygcheck.out file. Note that: 1 - absolute paths work OK for an scp pathname 2 - the "scp /tmp/foo bcserver:foobar" command works OK in win11's PowerShell 3 - the scp target host (bcserver) is a FreeBSD 12 OS running in a TrueNAS "jail".