diff --git a/changelogs/fragments/fileglob_fixes.yml b/changelogs/fragments/fileglob_fixes.yml
new file mode 100644
index 00000000000..c0a12b07348
--- /dev/null
+++ b/changelogs/fragments/fileglob_fixes.yml
@@ -0,0 +1,2 @@
+bugfixes:
+    - deal with cases in which just a file is pased and not a path with directories, now fileglob correctly searches in 'files/' subdirs.
diff --git a/lib/ansible/plugins/lookup/fileglob.py b/lib/ansible/plugins/lookup/fileglob.py
index 91442dda5e1..2460ba15ddd 100644
--- a/lib/ansible/plugins/lookup/fileglob.py
+++ b/lib/ansible/plugins/lookup/fileglob.py
@@ -58,8 +58,22 @@ class LookupModule(LookupBase):
         ret = []
         for term in terms:
             term_file = os.path.basename(term)
-            dwimmed_path = self.find_file_in_search_path(variables, 'files', os.path.dirname(term))
-            if dwimmed_path:
+            found_paths = []
+            if term_file != term:
+                found_paths.append(self.find_file_in_search_path(variables, 'files', os.path.dirname(term)))
+            else:
+                # no dir, just file, so use paths and 'files' paths instead
+                if 'ansible_search_path' in variables:
+                    paths = variables['ansible_search_path']
+                else:
+                    paths = [self.get_basedir(variables)]
+                for p in paths:
+                    found_paths.append(os.path.join(p, 'files'))
+                    found_paths.append(p)
+
+            for dwimmed_path in found_paths:
                 globbed = glob.glob(to_bytes(os.path.join(dwimmed_path, term_file), errors='surrogate_or_strict'))
                 ret.extend(to_text(g, errors='surrogate_or_strict') for g in globbed if os.path.isfile(g))
+                if ret:
+                    break
         return ret
diff --git a/test/integration/targets/fileglob/aliases b/test/integration/targets/fileglob/aliases
new file mode 100644
index 00000000000..a6dafcf8cd8
--- /dev/null
+++ b/test/integration/targets/fileglob/aliases
@@ -0,0 +1 @@
+shippable/posix/group1
diff --git a/test/integration/targets/fileglob/find_levels/files/play_adj_subdir.txt b/test/integration/targets/fileglob/find_levels/files/play_adj_subdir.txt
new file mode 100644
index 00000000000..50255880719
--- /dev/null
+++ b/test/integration/targets/fileglob/find_levels/files/play_adj_subdir.txt
@@ -0,0 +1 @@
+in files subdir adjacent to play
diff --git a/test/integration/targets/fileglob/find_levels/files/somepath/play_adj_subsubdir.txt b/test/integration/targets/fileglob/find_levels/files/somepath/play_adj_subsubdir.txt
new file mode 100644
index 00000000000..96c7a549362
--- /dev/null
+++ b/test/integration/targets/fileglob/find_levels/files/somepath/play_adj_subsubdir.txt
@@ -0,0 +1 @@
+in play adjacent subdir of files/
diff --git a/test/integration/targets/fileglob/find_levels/play.yml b/test/integration/targets/fileglob/find_levels/play.yml
new file mode 100644
index 00000000000..4bdee05de38
--- /dev/null
+++ b/test/integration/targets/fileglob/find_levels/play.yml
@@ -0,0 +1,13 @@
+- hosts: localhost
+  gather_facts: false
+  vars:
+    expected:
+        play_adj: ajectent to play
+        play_adj_subdir: in files subdir adjacent to play
+        somepath/play_adj_subsubdir: in play adjacent subdir of files/
+        in_role: file in role
+        otherpath/in_role_subdir: file in role subdir
+  tasks:
+    - name: Import role lookup
+      import_role:
+        name: get_file
diff --git a/test/integration/targets/fileglob/find_levels/play_adj.txt b/test/integration/targets/fileglob/find_levels/play_adj.txt
new file mode 100644
index 00000000000..14f0cf502bc
--- /dev/null
+++ b/test/integration/targets/fileglob/find_levels/play_adj.txt
@@ -0,0 +1 @@
+ajectent to play
diff --git a/test/integration/targets/fileglob/find_levels/roles/get_file/files/in_role.txt b/test/integration/targets/fileglob/find_levels/roles/get_file/files/in_role.txt
new file mode 100644
index 00000000000..fdfc9476c8a
--- /dev/null
+++ b/test/integration/targets/fileglob/find_levels/roles/get_file/files/in_role.txt
@@ -0,0 +1 @@
+file in role
diff --git a/test/integration/targets/fileglob/find_levels/roles/get_file/files/otherpath/in_role_subdir.txt b/test/integration/targets/fileglob/find_levels/roles/get_file/files/otherpath/in_role_subdir.txt
new file mode 100644
index 00000000000..40e75a40db5
--- /dev/null
+++ b/test/integration/targets/fileglob/find_levels/roles/get_file/files/otherpath/in_role_subdir.txt
@@ -0,0 +1 @@
+file in role subdir
diff --git a/test/integration/targets/fileglob/find_levels/roles/get_file/tasks/main.yml b/test/integration/targets/fileglob/find_levels/roles/get_file/tasks/main.yml
new file mode 100644
index 00000000000..2fc21df70df
--- /dev/null
+++ b/test/integration/targets/fileglob/find_levels/roles/get_file/tasks/main.yml
@@ -0,0 +1,10 @@
+- name: show file contents
+  debug:
+    msg: '{{ q("fileglob", seed + ".*") }}'
+  register: found
+
+- name: did we get right one?
+  assert:
+    that:
+        - found['msg'][0].endswith(seed + '.txt')
+        - q('file', found['msg'][0])[0] == expected[seed]
diff --git a/test/integration/targets/fileglob/runme.sh b/test/integration/targets/fileglob/runme.sh
new file mode 100755
index 00000000000..1ca7e1b7adf
--- /dev/null
+++ b/test/integration/targets/fileglob/runme.sh
@@ -0,0 +1,9 @@
+#!/usr/bin/env bash
+
+set -eux
+
+# fun multilevel finds
+for seed in play_adj play_adj_subdir somepath/play_adj_subsubdir in_role otherpath/in_role_subdir
+do
+	ansible-playbook find_levels/play.yml -e "seed='${seed}'" "$@"
+done