diff --git a/documentation/asciidoc/services/connect/use.adoc b/documentation/asciidoc/services/connect/use.adoc
index 4913484ab..8217fea48 100644
--- a/documentation/asciidoc/services/connect/use.adoc
+++ b/documentation/asciidoc/services/connect/use.adoc
@@ -103,7 +103,7 @@ image::images/screen-sharing-end.png[width="80%"]
 
 To turn off screen sharing, click the Connect system tray icon and unselect **Allow screen sharing**.  Your Raspberry Pi remains signed into Connect, but you won't be able to create a screen sharing session from the Connect dashboard.
 
-image:images/screen-sharing-disabled-desktop.png[width="80%"]
+image::images/screen-sharing-disabled-desktop.png[width="80%"]
 
 Alternatively, you can disable screen sharing with the following command:
 
@@ -168,7 +168,7 @@ image::images/remote-shell-end.png[width="80%"]
 
 To turn off remote shell access, click the Connect system tray icon and unselect **Allow remote shell**. Your Raspberry Pi remains signed into Connect, but you won't be able to create a remote shell session from the Connect dashboard.
 
-image:images/remote-shell-disabled-desktop.png[width="80%"]
+image::images/remote-shell-disabled-desktop.png[width="80%"]
 
 Alternatively, you can disable remote shell access with the following command:
 
diff --git a/scripts/create_build_adoc.py b/scripts/create_build_adoc.py
index da5d29314..536446645 100755
--- a/scripts/create_build_adoc.py
+++ b/scripts/create_build_adoc.py
@@ -21,7 +21,6 @@ def check_no_markdown(filename):
         if re.search(r'(\[.+?\]\(.+?\))', asciidoc):
             raise Exception("{} contains a Markdown-style link (i.e. '[title](url)' rather than 'url[title]')".format(filename))
 
-
 if __name__ == "__main__":
     index_json = sys.argv[1]
     config_yaml = sys.argv[2]
@@ -72,6 +71,12 @@ def check_no_markdown(filename):
                 m = re.match(r'^(include::)(.+)(\[\]\n?)$', line)
                 if m:
                     line = m.group(1) + os.path.join('{includedir}/{parentdir}', m.group(2)) + m.group(3)
+                # find all image references, append md5 hash at end to bust the cache if we change the image
+                m = re.match(r'^(image::)(.+)(\[(.+)]\n?)$', line)
+                if m:
+                    directory = os.path.dirname(os.path.abspath(src_adoc))
+                    image_hash = hashlib.md5(open(os.path.join(directory, m.group(2)),'rb').read()).hexdigest()
+                    line = m.group(1) + m.group(2) + '?hash=' + image_hash + m.group(3) + "\n"
             new_contents += line
 
     with open(build_adoc, 'w') as out_fh:
diff --git a/scripts/create_build_adoc_include.py b/scripts/create_build_adoc_include.py
index ab7c3c0cf..52227ebce 100755
--- a/scripts/create_build_adoc_include.py
+++ b/scripts/create_build_adoc_include.py
@@ -4,6 +4,7 @@
 import os
 import re
 import yaml
+import hashlib
 
 
 def check_no_markdown(filename):
@@ -48,6 +49,13 @@ def check_no_markdown(filename):
                     seen_header = True
                     if github_edit is not None:
                         line += edit_text + "\n\n"
+            else:
+                # find all image references, append md5 hash at end to bust the cache if we change the image
+                m = re.match(r'^(image::)(.+)(\[(.+)]\n?)$', line)
+                if m:
+                    directory = os.path.dirname(os.path.abspath(src_adoc))
+                    image_hash = hashlib.md5(open(os.path.join(directory, m.group(2)),'rb').read()).hexdigest()
+                    line = m.group(1) + m.group(2) + '?hash=' + image_hash + m.group(3) + "\n"
             new_contents += line
 
         with open(build_adoc, 'w') as out_fh: