diff --git a/docs/changes/5.3.3.md b/docs/changes/5.3.3.md
index 3f85fecd63..20896bb2b1 100644
--- a/docs/changes/5.3.3.md
+++ b/docs/changes/5.3.3.md
@@ -5,6 +5,7 @@ Release date: `2023-xx-xx`
 ## Core
 
 - [NXDRIVE-2828](https://jira.nuxeo.com/browse/NXDRIVE-2828): Remove sensitive information from Drive logs
+- [NXDRIVE-2861](https://jira.nuxeo.com/browse/NXDRIVE-2861): Fix behavior when not entering the correct URL format
 
 ### Direct Edit
 
diff --git a/nxdrive/gui/api.py b/nxdrive/gui/api.py
index 5e3f4372ba..fef78cffcf 100644
--- a/nxdrive/gui/api.py
+++ b/nxdrive/gui/api.py
@@ -784,6 +784,10 @@ def web_authentication(
             return
 
         # Handle the server URL
+        if "login.jsp" in server_url:
+            self.setMessage.emit("CONNECTION_ERROR", "error")
+            return
+
         error = ""
         try:
             error = self._get_ssl_error(server_url)
diff --git a/tests/functional/test_api.py b/tests/functional/test_api.py
new file mode 100644
index 0000000000..a1d7a14ead
--- /dev/null
+++ b/tests/functional/test_api.py
@@ -0,0 +1,34 @@
+from collections import namedtuple
+from unittest.mock import patch
+
+from nxdrive.gui.api import QMLDriveApi
+
+
+def test_web_authentication(manager_factory, nuxeo_url):
+    manager = manager_factory(with_engine=False)
+    manager.application = ""
+
+    def func(*args):
+        return True
+
+    def mocked_open_authentication_dialog():
+        return
+
+    Mocked_App = namedtuple(
+        "app",
+        "manager, open_authentication_dialog",
+        defaults=(manager, mocked_open_authentication_dialog),
+    )
+    app = Mocked_App()
+
+    drive_api = QMLDriveApi(app)
+
+    with manager:
+        with patch.object(manager, "check_local_folder_available", new=func):
+            url = f"{nuxeo_url}/login.jsp?requestedUrl=ui%2F"
+            returned_val = drive_api.web_authentication(
+                url,
+                "/dummy-path",
+                True,
+            )
+            assert not returned_val