diff --git a/changelogs/fragments/get_url-remove-fragile-code.yaml b/changelogs/fragments/get_url-remove-fragile-code.yaml
new file mode 100644
index 00000000000..ab997c576cc
--- /dev/null
+++ b/changelogs/fragments/get_url-remove-fragile-code.yaml
@@ -0,0 +1,2 @@
+bugfixes:
+  - get_url - improve code that parses checksums from a file so it is not fragile and reports a helpful error when no matching checksum is found
diff --git a/lib/ansible/modules/net_tools/basics/get_url.py b/lib/ansible/modules/net_tools/basics/get_url.py
index eb63a5791fa..53c79536a45 100644
--- a/lib/ansible/modules/net_tools/basics/get_url.py
+++ b/lib/ansible/modules/net_tools/basics/get_url.py
@@ -445,11 +445,22 @@ def main():
                 checksum_url = checksum
                 # download checksum file to checksum_tmpsrc
                 checksum_tmpsrc, checksum_info = url_get(module, checksum_url, dest, use_proxy, last_mod_time, force, timeout, headers, tmp_dest)
-                lines = [line.rstrip('\n') for line in open(checksum_tmpsrc)]
+                with open(checksum_tmpsrc) as f:
+                    lines = [line.rstrip('\n') for line in f]
                 os.remove(checksum_tmpsrc)
                 lines = dict(s.split(None, 1) for s in lines)
                 filename = url_filename(url)
-                [checksum] = (k for (k, v) in lines.items() if v.strip('./') == filename)
+
+                # Look through each line in the checksum file for a hash corresponding to
+                # the filename in the url, returning the first hash that is found.
+                for cksum in (s for (s, f) in lines.items() if f.strip('./') == filename):
+                    checksum = cksum
+                    break
+                else:
+                    checksum = None
+
+                if checksum is None:
+                    module.fail_json("Unable to find a checksum for file '%s' in '%s'" % (filename, checksum_url))
             # Remove any non-alphanumeric characters, including the infamous
             # Unicode zero-width space
             checksum = re.sub(r'\W+', '', checksum).lower()