diff --git a/src/calibre/srv/manage_users_cli.py b/src/calibre/srv/manage_users_cli.py
index bd19331e09..719dbe2a1e 100644
--- a/src/calibre/srv/manage_users_cli.py
+++ b/src/calibre/srv/manage_users_cli.py
@@ -8,7 +8,7 @@ import sys
 from functools import partial
 
 from calibre import prints
-from calibre.constants import preferred_encoding
+from calibre.constants import preferred_encoding, iswindows
 
 # Manage users CLI {{{
 
@@ -70,16 +70,41 @@ def manage_users_cli(path=None):
         return get_valid(_('Enter the username'), validate)
 
     def get_pass(username):
+
+        def getpass(prompt):
+            if iswindows:
+                # getpass is broken on windows with python 2.x and unicode, the
+                # below implementation is from the python 3 source code
+                import msvcrt
+                for c in prompt:
+                    msvcrt.putwch(c)
+                pw = ""
+                while 1:
+                    c = msvcrt.getwch()
+                    if c == '\r' or c == '\n':
+                        break
+                    if c == '\003':
+                        raise KeyboardInterrupt
+                    if c == '\b':
+                        pw = pw[:-1]
+                    else:
+                        pw = pw + c
+                msvcrt.putwch('\r')
+                msvcrt.putwch('\n')
+                return pw
+            else:
+                from getpass import getpass
+                return getpass(prompt).decode(enc)
+
         while True:
-            from getpass import getpass
             one = getpass(
-                _('Enter the new password for %s: ') % username).decode(enc)
+                _('Enter the new password for %s: ') % username)
             if not one:
                 prints(_('Empty passwords are not allowed'))
                 continue
             two = getpass(
                 _('Re-enter the new password for %s, to verify: ') % username
-            ).decode(enc)
+            )
             if one != two:
                 prints(_('Passwords do not match'))
                 continue