diff --git a/ironic/common/images.py b/ironic/common/images.py
index 2b52b789b2..aa883ada3b 100644
--- a/ironic/common/images.py
+++ b/ironic/common/images.py
@@ -657,10 +657,24 @@ def is_source_a_path(ctx, image_source):
         # NOTE(TheJulia): I don't really like this pattern, *but*
         # the wholedisk image support is similar.
         return
+    # NOTE(TheJulia): Files should have been caught almost exclusively
+    # before with the Content-Length check.
+    # When the ISO is mounted and the webserver mount point url is
+    # checked here, it has both 'Content-Length' and 'Content-Type'
+    # due to which it always returns False. Hence switched the conditions.
+    if ('Content-Type' in headers
+            and str(headers['Content-Type']).startswith('text/html')):
+        LOG.debug('Evaluated %(url)s to determine if it is a URL to a path '
+                  'or a file. A Content-Type header was returned with a text '
+                  'content, which suggests a file list was returned.',
+                  {'url': image_source})
+        return True
     # When issuing a head request, folders have no length
     # A list can be generated by the server.. This is a solid
     # hint.
-    if 'Content-Length' in headers:
+    if ('Content-Type' in headers
+            and (str(headers['Content-Type']) != 'text/html')
+            and 'Content-Length' in headers):
         LOG.debug('Evaluated %(url)s to determine if it is a URL to a path '
                   'or a file. A Content-Length header was returned '
                   'suggesting file.',
@@ -668,16 +682,6 @@ def is_source_a_path(ctx, image_source):
         # NOTE(TheJulia): Files on a webserver have a length which is returned
         # when headres are queried.
         return False
-    if ('Content-Type' in headers
-        and str(headers['Content-Type']).startswith('text')
-        and 'Content-Length' not in headers):
-        LOG.debug('Evaluated %(url)s to determine if it is a URL to a path '
-                  'or a file. A Content-Type header was returned with a text '
-                  'content, which suggests a file list was returned.',
-                  {'url': image_source})
-        return True
-        # NOTE(TheJulia): Files should have been caught almost exclusively
-        # before with the Content-Length check.
     if image_source.endswith('/'):
         # If all else fails, looks like a URL, and the server didn't give
         # us any hints.
diff --git a/ironic/tests/unit/common/test_images.py b/ironic/tests/unit/common/test_images.py
index dd782c687a..5530feb38c 100644
--- a/ironic/tests/unit/common/test_images.py
+++ b/ironic/tests/unit/common/test_images.py
@@ -318,7 +318,8 @@ class IronicImagesTestCase(base.TestCase):
                        autospec=True)
     def test_is_source_a_path_content_length(self, validate_mock):
         mock_response = mock.Mock()
-        mock_response.headers = {'Content-Length': 1}
+        mock_response.headers = {'Content-Length': 1,
+                                 'Content-Type': 'text/plain'}
         validate_mock.return_value = mock_response
         self.assertFalse(images.is_source_a_path('context', 'http://foo/bar/'))
         validate_mock.assert_called_once_with(mock.ANY, 'http://foo/bar/')
diff --git a/releasenotes/notes/fix_anaconda-70f4268edc255ff4.yaml b/releasenotes/notes/fix_anaconda-70f4268edc255ff4.yaml
new file mode 100644
index 0000000000..3882a28207
--- /dev/null
+++ b/releasenotes/notes/fix_anaconda-70f4268edc255ff4.yaml
@@ -0,0 +1,5 @@
+---
+fixes:
+  - |
+    Fixes the URL based anaconda deployment for parsing the given ``image_source``
+    url.