diff --git a/docs/administration.md b/docs/administration.md
index 320ad7a9c..4daa446c5 100644
--- a/docs/administration.md
+++ b/docs/administration.md
@@ -267,6 +267,12 @@ The filenames generated by this command follow the format
 paperless to use `PAPERLESS_FILENAME_FORMAT` for exported filenames
 instead, specify `--use-filename-format`.
 
+!!! warning
+
+    If exporting with the file name format, there may be errors due to
+    your operating system's maximum path lengths.  Try adjusting the export
+    target or consider not using the filename format.
+
 ### Document importer {#importer}
 
 The document importer takes the export produced by the [Document
diff --git a/docs/advanced_usage.md b/docs/advanced_usage.md
index ef2cc28c2..61b1c072e 100644
--- a/docs/advanced_usage.md
+++ b/docs/advanced_usage.md
@@ -336,6 +336,13 @@ value.
     However, keep in mind that inside docker, if files get stored outside of
     the predefined volumes, they will be lost after a restart of paperless.
 
+!!! warning
+
+    When file naming handling, in particular when using `{tag_list}`,
+    you may run into the limits of your operating system's maximum
+    path lengths.  Files will retain the previous path instead and
+    the issue logged.
+
 ## Storage paths
 
 One of the best things in Paperless is that you can not only access the
@@ -392,7 +399,7 @@ structure as in the previous example above.
     If you adjust the format of an existing storage path, old documents
     don't get relocated automatically. You need to run the
     [document renamer](/administration#renamer) to
-    adjust their pathes.
+    adjust their paths.
 
 ## Celery Monitoring {#celery-monitoring}