diff --git a/files/assets/js/markdown.js b/files/assets/js/markdown.js
index 7bd625f1aa..6e4039979d 100644
--- a/files/assets/js/markdown.js
+++ b/files/assets/js/markdown.js
@@ -54,7 +54,7 @@ marked.use({
 const reDisableBeforeUnload = /^\/submit|^\/h\/[a-zA-Z0-9_\-]{3,20}\/submit/;
 
 const image_regex_extensions = document.getElementById('IMAGE_FORMATS').value.replaceAll(',', '|')
-const regex_pattern = String.raw`(^|\s)(https:\/\/[\w\-.#&/=\?@%;+,:]{5,250}(\.|\?format=)(` + image_regex_extensions + String.raw`)((\?|&)[\w\-.#&/=\?@%;+,:]*)?)($|\s)`
+const regex_pattern = String.raw`(^|\s)(https:\/\/[\w\-.#&/=\?@%;+,:]{5,250}(\.|\?format=)(` + image_regex_extensions + String.raw`)((\?|&)[\w\-.#&/=\?@%;+,:]*)?)(?=$|\s|<)`
 const compiled_regex = new RegExp(regex_pattern, "g");
 
 const approved_embed_hosts = document.getElementById('approved_embed_hosts').value.replace("{'", "").replace("'}", "").split("', '")
diff --git a/files/helpers/regex.py b/files/helpers/regex.py
index e1f1e42290..86917d2a88 100644
--- a/files/helpers/regex.py
+++ b/files/helpers/regex.py
@@ -105,7 +105,7 @@ audio_regex_extensions = '|'.join(AUDIO_FORMATS)
 audio_sub_regex = re.compile(f'(?<!")(https:\/\/({hosts})\/[\w:~,()\-.#&\/=?@%;+]*?\.({audio_regex_extensions}))' + NOT_IN_CODE_OR_LINKS, flags=re.A)
 
 image_regex_extensions = '|'.join(IMAGE_FORMATS)
-image_sub_regex = re.compile(f'(?<!")(https:\/\/[\w\-.#&/=\?@%;+,:]{{5,250}}(\.|\?format=)({image_regex_extensions})((\?|&)[\w\-.#&/=\?@%;+,:]*)?)(?=$|\s)' + NOT_IN_CODE_OR_LINKS, flags=re.I|re.A)
+image_sub_regex = re.compile(f'(?<!")(https:\/\/[\w\-.#&/=\?@%;+,:]{{5,250}}(\.|\?format=)({image_regex_extensions})((\?|&)[\w\-.#&/=\?@%;+,:]*)?)(?=$|\s|<)' + NOT_IN_CODE_OR_LINKS, flags=re.I|re.A)
 
 image_regex_extensions_no_gif = image_regex_extensions.replace('|gif', '')
 imgur_regex = re.compile(f'^(https:\/\/i\.imgur\.com\/[a-z0-9]+)\.({image_regex_extensions_no_gif})', flags=re.I|re.A)