diff --git a/src/calibre/db/cli/main.py b/src/calibre/db/cli/main.py
index be7fb79961..1a957e0820 100644
--- a/src/calibre/db/cli/main.py
+++ b/src/calibre/db/cli/main.py
@@ -94,10 +94,11 @@ def get_parser(usage):
     go.add_option(
         '--password',
         help=_('Password for connecting to a calibre Content server.'
-               ' To read the password from standard input, use the special value: {}.'
-               ' To read the password from a file, use: {}. The angle brackets in the'
-               ' above are required, remember to escape them or use quotes for your shell.').format(
-                   '<stdin>', '<f:/path/to/file>')
+               ' To read the password from standard input, use the special value: {0}.'
+               ' To read the password from a file, use: {1} (i.e. <f: followed by the full path to the file and a trailing >).'
+               ' The angle brackets in the above are required, remember to escape them or use quotes'
+               ' for your shell.').format(
+                   '<stdin>', '<f:C:/path/to/file>' if iswindows else '<f:/path/to/file>')
     )
 
     return parser