diff --git a/lib/email/sender.rb b/lib/email/sender.rb
index aafd834bfd0..456f2054c81 100644
--- a/lib/email/sender.rb
+++ b/lib/email/sender.rb
@@ -26,7 +26,8 @@ module Email
   class Sender
 
     def initialize(message, email_type, user = nil)
-      @message =  message
+      @message = message
+      @message_attachments_index = {}
       @email_type = email_type
       @user = user
     end
@@ -240,7 +241,7 @@ module Email
       # Embeds any of the secure images that have been attached inline,
       # removing the redaction notice.
       if SiteSetting.secure_media_allow_embed_images_in_emails
-        style.inline_secure_images(@message.attachments)
+        style.inline_secure_images(@message.attachments, @message_attachments_index)
       end
 
       @message.html_part.body = style.to_s
@@ -328,6 +329,7 @@ module Email
             Discourse.store.download(attached_upload).path
           end
 
+          @message_attachments_index[original_upload.sha1] = @message.attachments.size
           @message.attachments[original_upload.original_filename] = File.read(path)
           email_size += File.size(path)
         rescue => e
diff --git a/lib/email/styles.rb b/lib/email/styles.rb
index 5938dffaf47..c848ecf6159 100644
--- a/lib/email/styles.rb
+++ b/lib/email/styles.rb
@@ -253,7 +253,7 @@ module Email
       @@plugin_callbacks.each { |block| block.call(@fragment, @opts) }
     end
 
-    def inline_secure_images(attachments)
+    def inline_secure_images(attachments, attachments_index)
       stripped_media = @fragment.css('[data-stripped-secure-media]')
       upload_shas = {}
       stripped_media.each do |div|
@@ -269,10 +269,8 @@ module Email
         upload = uploads.find { |upl| upl.sha1 == upload_shas[div['data-stripped-secure-media']] }
         next if !upload
 
-        original_filename = upload.original_filename
-
-        if attachments[original_filename]
-          url = attachments[original_filename].url
+        if attachments[attachments_index[upload.sha1]]
+          url = attachments[attachments_index[upload.sha1]].url
 
           onebox_type = div['data-onebox-type']
           style = if onebox_type
diff --git a/spec/components/email/sender_spec.rb b/spec/components/email/sender_spec.rb
index 34c1a2e36a5..7d6643d9f2c 100644
--- a/spec/components/email/sender_spec.rb
+++ b/spec/components/email/sender_spec.rb
@@ -498,6 +498,21 @@ describe Email::Sender do
           SiteSetting.secure_media_allow_embed_images_in_emails = true
         end
 
+        it "can inline images with duplicate names" do
+          @secure_image_2 = UploadCreator.new(file_from_fixtures("logo-dev.png", "images"), "logo.png").create_for(Discourse.system_user.id)
+          @secure_image_2.update_secure_status(override: true)
+          @secure_image_2.update(access_control_post_id: reply.id)
+
+          Jobs::PullHotlinkedImages.any_instance.expects(:execute)
+          reply.update(raw: "#{UploadMarkdown.new(@secure_image).image_markdown}\n#{UploadMarkdown.new(@secure_image_2).image_markdown}")
+          reply.rebake!
+
+          Email::Sender.new(message, :valid_type).send
+          expect(message.attachments.size).to eq(2)
+          expect(message.to_s.scan(/cid:[\w\-@.]+/).length).to eq(2)
+          expect(message.to_s.scan(/cid:[\w\-@.]+/).uniq.length).to eq(2)
+        end
+
         it "does not attach images that are not marked as secure" do
           Email::Sender.new(message, :valid_type).send
           expect(message.attachments.length).to eq(4)
diff --git a/spec/components/email/styles_spec.rb b/spec/components/email/styles_spec.rb
index 55fe5187ef8..be5b634d54e 100644
--- a/spec/components/email/styles_spec.rb
+++ b/spec/components/email/styles_spec.rb
@@ -252,8 +252,9 @@ describe Email::Styles do
       SiteSetting.secure_media = true
     end
 
-    let(:attachments) { { 'testimage.png' => stub(url: 'cid:email/test.png') } }
     fab!(:upload) { Fabricate(:upload, original_filename: 'testimage.png', secure: true, sha1: '123456') }
+    let(:attachments) { [stub(url: 'cid:email/test.png')] }
+    let(:attachments_index) { { upload.sha1 => 0 } }
     let(:html) { "<a href=\"#{Discourse.base_url}\/secure-media-uploads/original/1X/123456.png\"><img src=\"/secure-media-uploads/original/1X/123456.png\" width=\"20\" height=\"30\"></a>" }
 
     def strip_and_inline
@@ -265,7 +266,7 @@ describe Email::Styles do
 
       # pass in the attachments to match uploads based on sha + original filename
       styler = Email::Styles.new(html)
-      styler.inline_secure_images(attachments)
+      styler.inline_secure_images(attachments, attachments_index)
       @frag = Nokogiri::HTML5.fragment(styler.to_s)
     end
 
@@ -302,12 +303,8 @@ describe Email::Styles do
       end
 
       let(:siteicon) { Fabricate(:upload, original_filename: "siteicon.ico") }
-      let(:attachments) do
-        {
-          'testimage.png' => stub(url: 'cid:email/test.png'),
-          'siteicon.ico' => stub(url: 'cid:email/test2.ico')
-        }
-      end
+      let(:attachments) { [stub(url: 'cid:email/test.png'), stub(url: 'cid:email/test2.ico')] }
+      let(:attachments_index) { { upload.sha1 => 0, siteicon.sha1 => 1 } }
       let(:html) do
         <<~HTML
 <aside class="onebox allowlistedgeneric">