diff --git a/app/models/upload.rb b/app/models/upload.rb
index 947481cb2fc..dccd90a1d86 100644
--- a/app/models/upload.rb
+++ b/app/models/upload.rb
@@ -168,6 +168,10 @@ class Upload < ActiveRecord::Base
     Digest::SHA1.file(path).hexdigest
   end
 
+  def self.extract_upload_url(url)
+    url.match(/(\/original\/\dX[\/\.\w]*\/([a-zA-Z0-9]+)[\.\w]*)/)
+  end
+
   def self.get_from_url(url)
     return if url.blank?
 
@@ -177,7 +181,7 @@ class Upload < ActiveRecord::Base
     end
 
     return if uri&.path.blank?
-    data = uri.path.match(/(\/original\/\dX[\/\.\w]*\/([a-zA-Z0-9]+)[\.\w]*)/)
+    data = extract_upload_url(uri.path)
     return if data.blank?
     sha1 = data[2]
     upload = nil
diff --git a/lib/upload_recovery.rb b/lib/upload_recovery.rb
index d2a584fa882..75b6e3e0421 100644
--- a/lib/upload_recovery.rb
+++ b/lib/upload_recovery.rb
@@ -8,18 +8,36 @@ class UploadRecovery
       begin
         analyzer = PostAnalyzer.new(post.raw, post.topic_id)
 
-        analyzer.cooked_stripped.css("img").each do |img|
-          if dom_class = img["class"]
-            if (Post.white_listed_image_classes & dom_class.split).count > 0
-              next
+        analyzer.cooked_stripped.css("img", "a").each do |media|
+          if media.name == "img"
+            if dom_class = media["class"]
+              if (Post.white_listed_image_classes & dom_class.split).count > 0
+                next
+              end
             end
-          end
 
-          if img["data-orig-src"]
-            if @dry_run
-              puts "#{post.full_url} #{img["data-orig-src"]}"
-            else
-              recover_post_upload(post, img["data-orig-src"])
+            orig_src = media["data-orig-src"]
+
+            if orig_src
+              if @dry_run
+                puts "#{post.full_url} #{orig_src}"
+              else
+                recover_post_upload(post, Upload.sha1_from_short_url(orig_src))
+              end
+            end
+          elsif media.name == "a"
+            href = media["href"]
+
+            if data = Upload.extract_upload_url(href)
+              sha1 = data[2]
+
+              unless upload = Upload.get_from_url(href)
+                if @dry_run
+                  puts "#{post.full_url} #{href}"
+                else
+                  recover_post_upload(post, sha1)
+                end
+              end
             end
           end
         end
@@ -32,8 +50,7 @@ class UploadRecovery
 
   private
 
-  def recover_post_upload(post, short_url)
-    sha1 = Upload.sha1_from_short_url(short_url)
+  def recover_post_upload(post, sha1)
     return unless sha1.present?
 
     attributes = {
diff --git a/spec/fixtures/pdf/small.pdf b/spec/fixtures/pdf/small.pdf
new file mode 100644
index 00000000000..9ec444cfa40
--- /dev/null
+++ b/spec/fixtures/pdf/small.pdf
@@ -0,0 +1,5 @@
+%PDF-1.
+1 0 obj<</Pages 2 0 R>>endobj
+2 0 obj<</Kids[3 0 R]/Count 1>>endobj
+3 0 obj<</Parent 2 0 R>>endobj
+trailer <</Root 1 0 R>>
\ No newline at end of file
diff --git a/spec/lib/upload_recovery_spec.rb b/spec/lib/upload_recovery_spec.rb
index 7a5929d8ffa..b28e04c192e 100644
--- a/spec/lib/upload_recovery_spec.rb
+++ b/spec/lib/upload_recovery_spec.rb
@@ -6,14 +6,24 @@ RSpec.describe UploadRecovery do
 
   let(:upload) do
     UploadCreator.new(
-      file_from_fixtures("logo.png"),
+      file_from_fixtures("smallest.png"),
       "logo.png"
     ).create_for(user.id)
   end
 
+  let(:upload2) do
+    UploadCreator.new(
+      file_from_fixtures("small.pdf", "pdf"),
+      "some.pdf"
+    ).create_for(user.id)
+  end
+
   let(:post) do
     Fabricate(:post,
-      raw: "![logo.png](#{upload.short_url})",
+      raw: <<~SQL,
+      ![logo.png](#{upload.short_url})
+      <a class="attachment" href="#{upload2.url}">some.pdf</a>
+      SQL
       user: user
     ).tap(&:link_post_uploads)
   end
@@ -21,17 +31,20 @@ RSpec.describe UploadRecovery do
   let(:upload_recovery) { UploadRecovery.new }
 
   before do
+    SiteSetting.authorized_extensions = 'png|pdf'
     SiteSetting.queue_jobs = false
   end
 
   describe '#recover' do
     after do
-      public_path = "#{Discourse.store.public_dir}#{upload.url}"
+      [upload, upload2].each do |u|
+        public_path = "#{Discourse.store.public_dir}#{u.url}"
 
-      [
-        public_path,
-        public_path.sub("uploads", "uploads/tombstone")
-      ].each { |path| File.delete(path) if File.exists?(path) }
+        [
+          public_path,
+          public_path.sub("uploads", "uploads/tombstone")
+        ].each { |path| File.delete(path) if File.exists?(path) }
+      end
     end
 
     describe 'when given an invalid sha1' do
@@ -54,17 +67,18 @@ RSpec.describe UploadRecovery do
       upload_recovery.recover(Post.where("updated_at >= ?", 1.day.ago))
     end
 
-    it 'should recover the upload' do
+    it 'should recover uploads and attachments' do
       stub_request(:get, "http://test.localhost#{upload.url}")
         .to_return(status: 200)
 
       expect do
         upload.destroy!
-      end.to change { post.reload.uploads.count }.from(1).to(0)
+        upload2.destroy!
+      end.to change { post.reload.uploads.count }.from(2).to(0)
 
       expect do
         upload_recovery.recover
-      end.to change { post.reload.uploads.count }.from(0).to(1)
+      end.to change { post.reload.uploads.count }.from(0).to(2)
     end
   end
 end