diff --git a/datalad/ui/dialog.py b/datalad/ui/dialog.py
index f43d6cc2b3..4d217fd454 100644
--- a/datalad/ui/dialog.py
+++ b/datalad/ui/dialog.py
@@ -31,7 +31,7 @@
 from ..utils import auto_repr
 from ..utils import on_windows
 from .base import InteractiveUI
-from .utils import has_terminal
+from .utils import can_prompt
 from datalad.support.exceptions import CapturedException
 
 # Example APIs which might be useful to look for "inspiration"
@@ -359,7 +359,7 @@ def get_progressbar(self, *args, **kwargs):
                 *args, **kwargs)
 
     def input(self, prompt, hidden=False):
-        if not has_terminal():
+        if not can_prompt():
             # we are not interactive
             raise RuntimeError('Interactive input not available for `ui.input()` in annex remotes')
         return super(UnderAnnexUI, self).input(prompt, hidden)
@@ -371,7 +371,7 @@ def question(self,
                  default=None,
                  hidden=False,
                  repeat=None):
-        if not has_terminal():
+        if not can_prompt():
             # we are not interactive
             raise RuntimeError('Interactive input not available for `ui.question()` in annex remotes')
         return super(UnderAnnexUI, self).question(
diff --git a/datalad/ui/utils.py b/datalad/ui/utils.py
index 2576bb2858..e3de1adf31 100644
--- a/datalad/ui/utils.py
+++ b/datalad/ui/utils.py
@@ -76,13 +76,17 @@ def show_hint(msg):
                 ansi_colors.YELLOW)))
 
 
-def has_terminal():
-    """Return True if the process has a controlling terminal
+def can_prompt() -> bool:
+    """Return True if the process can prompt for credentials
 
-    This checks for a controlling terminal on Linux
+    On Linux this method checks for a controlling terminal.
+    On Windows it always returns True.
     """
-    try:
-        open('/dev/tty', 'r').close()
+    if on_windows:
         return True
-    except (IOError, OSError):
-        return False
+    else:
+        try:
+            open('/dev/tty', 'r').close()
+            return True
+        except (IOError, OSError):
+            return False