diff --git a/tools/mpremote/mpremote/commands.py b/tools/mpremote/mpremote/commands.py
index 2b1acea43..f86befd08 100644
--- a/tools/mpremote/mpremote/commands.py
+++ b/tools/mpremote/mpremote/commands.py
@@ -129,8 +129,15 @@ def _remote_path_basename(a):
 
 def do_filesystem_cp(state, src, dest, multiple, check_hash=False):
     if dest.startswith(":"):
-        dest_exists = state.transport.fs_exists(dest[1:])
-        dest_isdir = dest_exists and state.transport.fs_isdir(dest[1:])
+        dest_no_slash = dest.rstrip("/" + os.path.sep + (os.path.altsep or ""))
+        dest_exists = state.transport.fs_exists(dest_no_slash[1:])
+        dest_isdir = dest_exists and state.transport.fs_isdir(dest_no_slash[1:])
+
+        # A trailing / on dest forces it to be a directory.
+        if dest != dest_no_slash:
+            if not dest_isdir:
+                raise CommandError("cp: destination is not a directory")
+            dest = dest_no_slash
     else:
         dest_exists = os.path.exists(dest)
         dest_isdir = dest_exists and os.path.isdir(dest)
diff --git a/tools/mpremote/tests/test_filesystem.sh b/tools/mpremote/tests/test_filesystem.sh
index 727efea90..afeb7c91d 100755
--- a/tools/mpremote/tests/test_filesystem.sh
+++ b/tools/mpremote/tests/test_filesystem.sh
@@ -71,6 +71,11 @@ echo -----
 $MPREMOTE resume cp -f "${TMP}/a.py" :aaa
 $MPREMOTE resume cat :aaa/a.py
 
+# Test cp where the destination has a trailing /.
+echo -----
+$MPREMOTE resume cp "${TMP}/a.py" :aaa/
+$MPREMOTE resume cp "${TMP}/a.py" :aaa/a.py/ || echo "expect error"
+
 echo -----
 $MPREMOTE resume rm :b.py c.py
 $MPREMOTE resume ls
diff --git a/tools/mpremote/tests/test_filesystem.sh.exp b/tools/mpremote/tests/test_filesystem.sh.exp
index b252bc7eb..82fe7d6bf 100644
--- a/tools/mpremote/tests/test_filesystem.sh.exp
+++ b/tools/mpremote/tests/test_filesystem.sh.exp
@@ -42,6 +42,12 @@ cp ${TMP}/a.py :aaa
 print("Hello")
 print("World")
 -----
+cp ${TMP}/a.py :aaa/
+Up to date: aaa/a.py
+cp ${TMP}/a.py :aaa/a.py/
+mpremote: cp: destination is not a directory
+expect error
+-----
 rm :b.py
 rm :c.py
 ls :