diff --git a/app/jobs/regular/pull_hotlinked_images.rb b/app/jobs/regular/pull_hotlinked_images.rb
index a42d45c08a1..46457fe8fc6 100644
--- a/app/jobs/regular/pull_hotlinked_images.rb
+++ b/app/jobs/regular/pull_hotlinked_images.rb
@@ -94,9 +94,17 @@ module Jobs
 
               replace_raw = ->(match, match_src, replacement, _index) {
                 if src.include?(match_src)
+
+                  replacement =
+                    if replacement.include?(InlineUploads::PLACEHOLDER)
+                      replacement.sub(InlineUploads::PLACEHOLDER, upload.short_url)
+                    elsif replacement.include?(InlineUploads::PATH_PLACEHOLDER)
+                      replacement.sub(InlineUploads::PATH_PLACEHOLDER, upload.short_path)
+                    end
+
                   raw = raw.gsub(
                     match,
-                    replacement.sub(InlineUploads::PLACEHOLDER, upload.short_url)
+                    replacement
                   )
                 end
               }
diff --git a/app/services/inline_uploads.rb b/app/services/inline_uploads.rb
index 6ac8ed5dbbf..bf42ac94e87 100644
--- a/app/services/inline_uploads.rb
+++ b/app/services/inline_uploads.rb
@@ -214,8 +214,8 @@ class InlineUploads
   end
 
   def self.match_img(markdown, external_src: false)
-    markdown.scan(/(<(?!img)[^<>]+\/?>)?(\n*)(([ ]*)<img ([^>\n]+)>([ ]*))(\n*)/) do |match|
-      node = Nokogiri::HTML::fragment(match[2].strip).children[0]
+    markdown.scan(/(([ ]*)<(?!img)[^<>]+\/?>)?(\n*)(([ ]*)<img ([^>\n]+)>([ ]*))(\n*)/) do |match|
+      node = Nokogiri::HTML::fragment(match[3].strip).children[0]
       src =  node.attributes["src"]&.value
 
       if src && (matched_uploads(src).present? || external_src)
@@ -228,24 +228,28 @@ class InlineUploads
 
         spaces_before =
           if after_html_tag && !match[0].end_with?("/>")
-            (match[3].length > 0 ? match[3] : "  ")
+            (match[4].length > 0 ? match[4] : "  ")
           else
             ""
           end
 
         replacement = +"#{spaces_before}![#{text}](#{PLACEHOLDER}#{title.present? ? " \"#{title}\"" : ""})"
 
-        if after_html_tag && (num_newlines = match[1].length) <= 1
+        if after_html_tag && (num_newlines = match[2].length) <= 1
           replacement.prepend("\n" * (num_newlines == 0 ? 2 : 1))
         end
 
-        if after_html_tag && !match[0].end_with?("/>") && (num_newlines = match[6].length) <= 1
+        if after_html_tag && !match[0].end_with?("/>") && (num_newlines = match[7].length) <= 1
           replacement += ("\n" * (num_newlines == 0 ? 2 : 1))
         end
 
-        match[2].strip! if !after_html_tag
+        match[3].strip! if !after_html_tag
 
-        yield(match[2], src, replacement, $~.offset(0)[0]) if block_given?
+        if match[1].nil? || match[1].length < 4
+          yield(match[3], src, replacement, $~.offset(0)[0]) if block_given?
+        else
+          yield(match[3], src, match[3].sub(src, PATH_PLACEHOLDER), $~.offset(0)[0]) if block_given?
+        end
       end
     end
   end
diff --git a/spec/jobs/pull_hotlinked_images_spec.rb b/spec/jobs/pull_hotlinked_images_spec.rb
index a1548fca3ea..cf3b2b4c6ee 100644
--- a/spec/jobs/pull_hotlinked_images_spec.rb
+++ b/spec/jobs/pull_hotlinked_images_spec.rb
@@ -57,7 +57,11 @@ describe Jobs::PullHotlinkedImages do
     end
 
     it 'replaces images in an anchor tag with weird indentation' do
+      stub_request(:get, "http://test.localhost/uploads/short-url/z2QSs1KJWoj51uYhDjb6ifCzxH6.gif")
+        .to_return(status: 200, body: "")
+
       post = Fabricate(:post, raw: <<~RAW)
+      <h1></h1>
                                 <a href="https://somelink.com">
                                     <img alt="somelink" src="#{image_url}" />
                                 </a>
@@ -67,11 +71,12 @@ describe Jobs::PullHotlinkedImages do
         Jobs::PullHotlinkedImages.new.execute(post_id: post.id)
       end.to change { Upload.count }.by(1)
 
+      upload = post.uploads.last
+
       expect(post.reload.raw).to eq(<<~RAW.chomp)
+      <h1></h1>
                                 <a href="https://somelink.com">
-
-                                    ![somelink](#{post.uploads.last.short_url})
-
+                                    <img alt="somelink" src="#{upload.short_path}" />
                                 </a>
       RAW
     end
diff --git a/spec/services/inline_uploads_spec.rb b/spec/services/inline_uploads_spec.rb
index d54666f1831..82ad449a9e7 100644
--- a/spec/services/inline_uploads_spec.rb
+++ b/spec/services/inline_uploads_spec.rb
@@ -303,17 +303,36 @@ RSpec.describe InlineUploads do
         MD
       end
 
+      it "should correctly update images sources within anchor tags with indentation" do
+        md = <<~MD
+        <h1></h1>
+                        <a href="http://somelink.com">
+                          <img src="#{upload2.url}" alt="test" width="500" height="500">
+                        </a>
+
+                        <a href="http://somelink.com">
+                          <img src="#{upload2.url}" alt="test" width="500" height="500">
+                        </a>
+        MD
+
+        expect(InlineUploads.process(md)).to eq(<<~MD)
+        <h1></h1>
+                        <a href="http://somelink.com">
+                          <img src="#{upload2.short_path}" alt="test" width="500" height="500">
+                        </a>
+
+                        <a href="http://somelink.com">
+                          <img src="#{upload2.url}" alt="test" width="500" height="500">
+                        </a>
+        MD
+      end
+
       it "should correctly update image sources within anchor or paragraph tags" do
         md = <<~MD
         <a href="http://somelink.com">
           <img src="#{upload.url}" alt="test" width="500" height="500">
         </a>
 
-        <h1></h1>
-                        <a href="http://somelink.com">
-                          <img src="#{upload2.url}" alt="test" width="500" height="500">
-                        </a>
-
         <p>
           <img src="#{upload2.url}" alt="test">
         </p>
@@ -342,13 +361,6 @@ RSpec.describe InlineUploads do
 
         </a>
 
-        <h1></h1>
-                        <a href="http://somelink.com">
-
-                          ![test|500x500](#{upload2.short_url})
-
-                        </a>
-
         <p>
 
           ![test](#{upload2.short_url})