diff --git a/app/models/upload.rb b/app/models/upload.rb
index 86bf760b8da..249c50f4be4 100644
--- a/app/models/upload.rb
+++ b/app/models/upload.rb
@@ -100,6 +100,10 @@ class Upload < ActiveRecord::Base
     self.url
   end
 
+  def to_markdown
+    UploadMarkdown.new(self).to_markdown
+  end
+
   def thumbnail(width = self.thumbnail_width, height = self.thumbnail_height)
     optimized_images.find_by(width: width, height: height)
   end
diff --git a/app/models/upload_reference.rb b/app/models/upload_reference.rb
index 73de830f545..ea5401e1233 100644
--- a/app/models/upload_reference.rb
+++ b/app/models/upload_reference.rb
@@ -4,6 +4,8 @@ class UploadReference < ActiveRecord::Base
   belongs_to :upload
   belongs_to :target, polymorphic: true
 
+  delegate :to_markdown, to: :upload
+
   def self.ensure_exist!(upload_ids: [], target: nil, target_type: nil, target_id: nil)
     if !target && !(target_type && target_id)
       raise "target OR target_type and target_id are required"
diff --git a/plugins/chat/app/jobs/regular/chat_channel_delete.rb b/plugins/chat/app/jobs/regular/chat_channel_delete.rb
index ac89be4db99..3d407caf9cd 100644
--- a/plugins/chat/app/jobs/regular/chat_channel_delete.rb
+++ b/plugins/chat/app/jobs/regular/chat_channel_delete.rb
@@ -28,24 +28,30 @@ module Jobs
         Rails.logger.debug(
           "Deleting chat messages, mentions, revisions, and uploads for channel #{chat_channel.id}",
         )
-        ChatMessage.transaction do
-          chat_messages = ChatMessage.where(chat_channel: chat_channel)
-          message_ids = chat_messages.select(:id)
-          ChatMention.where(chat_message_id: message_ids).delete_all
-          ChatMessageRevision.where(chat_message_id: message_ids).delete_all
-          ChatMessageReaction.where(chat_message_id: message_ids).delete_all
+        chat_messages = ChatMessage.where(chat_channel: chat_channel)
+        delete_messages_and_related_records(chat_channel, chat_messages) if chat_messages.any?
+      end
+    end
 
-          # if the uploads are not used anywhere else they will be deleted
-          # by the CleanUpUploads job in core
-          ChatUpload.where(chat_message_id: message_ids).delete_all
+    def delete_messages_and_related_records(chat_channel, chat_messages)
+      message_ids = chat_messages.pluck(:id)
 
-          # only the messages and the channel are Trashable, everything else gets
-          # permanently destroyed
-          chat_messages.update_all(
-            deleted_by_id: chat_channel.deleted_by_id,
-            deleted_at: Time.zone.now,
-          )
-        end
+      ChatMessage.transaction do
+        ChatMention.where(chat_message_id: message_ids).delete_all
+        ChatMessageRevision.where(chat_message_id: message_ids).delete_all
+        ChatMessageReaction.where(chat_message_id: message_ids).delete_all
+
+        # if the uploads are not used anywhere else they will be deleted
+        # by the CleanUpUploads job in core
+        DB.exec("DELETE FROM chat_uploads WHERE chat_message_id IN (#{message_ids.join(",")})")
+        UploadReference.where(target_id: message_ids, target_type: "ChatMessage").delete_all
+
+        # only the messages and the channel are Trashable, everything else gets
+        # permanently destroyed
+        chat_messages.update_all(
+          deleted_by_id: chat_channel.deleted_by_id,
+          deleted_at: Time.zone.now,
+        )
       end
     end
   end
diff --git a/plugins/chat/app/models/chat_message.rb b/plugins/chat/app/models/chat_message.rb
index f7688a8a13d..79e938b55b0 100644
--- a/plugins/chat/app/models/chat_message.rb
+++ b/plugins/chat/app/models/chat_message.rb
@@ -14,8 +14,11 @@ class ChatMessage < ActiveRecord::Base
   has_many :revisions, class_name: "ChatMessageRevision", dependent: :destroy
   has_many :reactions, class_name: "ChatMessageReaction", dependent: :destroy
   has_many :bookmarks, as: :bookmarkable, dependent: :destroy
+  has_many :upload_references, as: :target, dependent: :destroy
+  has_many :uploads, through: :upload_references
+
+  # TODO (martin) Remove this when we drop the ChatUpload table
   has_many :chat_uploads, dependent: :destroy
-  has_many :uploads, through: :chat_uploads
   has_one :chat_webhook_event, dependent: :destroy
   has_one :chat_mention, dependent: :destroy
 
@@ -61,14 +64,20 @@ class ChatMessage < ActiveRecord::Base
   end
 
   def attach_uploads(uploads)
-    return if uploads.blank?
+    return if uploads.blank? || self.new_record?
 
     now = Time.now
-    record_attrs =
+    ref_record_attrs =
       uploads.map do |upload|
-        { upload_id: upload.id, chat_message_id: self.id, created_at: now, updated_at: now }
+        {
+          upload_id: upload.id,
+          target_id: self.id,
+          target_type: "ChatMessage",
+          created_at: now,
+          updated_at: now,
+        }
       end
-    ChatUpload.insert_all!(record_attrs)
+    UploadReference.insert_all!(ref_record_attrs)
   end
 
   def excerpt
@@ -91,20 +100,19 @@ class ChatMessage < ActiveRecord::Base
   end
 
   def to_markdown
-    markdown = []
+    upload_markdown =
+      self
+        .upload_references
+        .includes(:upload)
+        .order(:created_at)
+        .map(&:to_markdown)
+        .reject(&:empty?)
 
-    if self.message.present?
-      msg = self.message
+    return self.message if upload_markdown.empty?
 
-      self.chat_uploads.any? ? markdown << msg + "\n" : markdown << msg
-    end
+    return ["#{self.message}\n"].concat(upload_markdown).join("\n") if self.message.present?
 
-    self
-      .chat_uploads
-      .order(:created_at)
-      .each { |chat_upload| markdown << UploadMarkdown.new(chat_upload.upload).to_markdown }
-
-    markdown.reject(&:empty?).join("\n")
+    upload_markdown.join("\n")
   end
 
   def cook
diff --git a/plugins/chat/app/models/chat_upload.rb b/plugins/chat/app/models/chat_upload.rb
index 3382328bfd7..f9d969c40af 100644
--- a/plugins/chat/app/models/chat_upload.rb
+++ b/plugins/chat/app/models/chat_upload.rb
@@ -1,8 +1,15 @@
 # frozen_string_literal: true
 
+# TODO (martin) DEPRECATED: Remove this model once UploadReference has been
+# in place for a couple of months, 2023-04-01
+#
+# NOTE: Do not use this model anymore, chat messages are linked to uploads via
+# the UploadReference table now, just like everything else.
 class ChatUpload < ActiveRecord::Base
   belongs_to :chat_message
   belongs_to :upload
+
+  deprecate *public_instance_methods(false)
 end
 
 # == Schema Information
diff --git a/plugins/chat/db/migrate/20230123020036_move_chat_uploads_to_upload_references.rb b/plugins/chat/db/migrate/20230123020036_move_chat_uploads_to_upload_references.rb
new file mode 100644
index 00000000000..22dafbcff20
--- /dev/null
+++ b/plugins/chat/db/migrate/20230123020036_move_chat_uploads_to_upload_references.rb
@@ -0,0 +1,17 @@
+# frozen_string_literal: true
+
+class MoveChatUploadsToUploadReferences < ActiveRecord::Migration[7.0]
+  def up
+    execute <<~SQL
+      INSERT INTO upload_references(upload_id, target_type, target_id, created_at, updated_at)
+      SELECT chat_uploads.upload_id, 'ChatMessage', chat_uploads.chat_message_id, chat_uploads.created_at, chat_uploads.updated_at
+      FROM chat_uploads
+      INNER JOIN uploads ON uploads.id = chat_uploads.upload_id
+      ON CONFLICT DO NOTHING
+    SQL
+  end
+
+  def down
+    raise ActiveRecord::IrreversibleMigration
+  end
+end
diff --git a/plugins/chat/db/post_migrate/20230123025112_move_chat_uploads_to_upload_references_post.rb b/plugins/chat/db/post_migrate/20230123025112_move_chat_uploads_to_upload_references_post.rb
new file mode 100644
index 00000000000..02ec2dfbffe
--- /dev/null
+++ b/plugins/chat/db/post_migrate/20230123025112_move_chat_uploads_to_upload_references_post.rb
@@ -0,0 +1,17 @@
+# frozen_string_literal: true
+
+class MoveChatUploadsToUploadReferencesPost < ActiveRecord::Migration[7.0]
+  def up
+    execute <<~SQL
+      INSERT INTO upload_references(upload_id, target_type, target_id, created_at, updated_at)
+      SELECT chat_uploads.upload_id, 'ChatMessage', chat_uploads.chat_message_id, chat_uploads.created_at, chat_uploads.updated_at
+      FROM chat_uploads
+      INNER JOIN uploads ON uploads.id = chat_uploads.upload_id
+      ON CONFLICT DO NOTHING
+    SQL
+  end
+
+  def down
+    raise ActiveRecord::IrreversibleMigration
+  end
+end
diff --git a/plugins/chat/lib/chat_message_updater.rb b/plugins/chat/lib/chat_message_updater.rb
index 04e8ae9372b..79ecfed4e2c 100644
--- a/plugins/chat/lib/chat_message_updater.rb
+++ b/plugins/chat/lib/chat_message_updater.rb
@@ -83,7 +83,8 @@ class Chat::ChatMessageUpdater
   def update_uploads(upload_info)
     return unless upload_info[:changed]
 
-    ChatUpload.where(chat_message: @chat_message).destroy_all
+    DB.exec("DELETE FROM chat_uploads WHERE chat_message_id = #{@chat_message.id}")
+    UploadReference.where(target: @chat_message).destroy_all
     @chat_message.attach_uploads(upload_info[:uploads])
   end
 
diff --git a/plugins/chat/lib/chat_transcript_service.rb b/plugins/chat/lib/chat_transcript_service.rb
index 6326494cdde..f61421d35f6 100644
--- a/plugins/chat/lib/chat_transcript_service.rb
+++ b/plugins/chat/lib/chat_transcript_service.rb
@@ -147,7 +147,7 @@ class ChatTranscriptService
   def messages
     @messages ||=
       ChatMessage
-        .includes(:user, chat_uploads: :upload)
+        .includes(:user, upload_references: :upload)
         .where(id: @message_ids, chat_channel_id: @channel.id)
         .order(:created_at)
   end
diff --git a/plugins/chat/lib/message_mover.rb b/plugins/chat/lib/message_mover.rb
index fc290f757ca..11cd84ac33d 100644
--- a/plugins/chat/lib/message_mover.rb
+++ b/plugins/chat/lib/message_mover.rb
@@ -125,10 +125,10 @@ class Chat::MessageMover
     SQL
 
     DB.exec(<<~SQL)
-      UPDATE chat_uploads cu
-      SET chat_message_id = mm.new_chat_message_id
+      UPDATE upload_references uref
+      SET target_id = mm.new_chat_message_id
       FROM moved_chat_messages mm
-      WHERE cu.chat_message_id = mm.old_chat_message_id
+      WHERE uref.target_id = mm.old_chat_message_id AND uref.target_type = 'ChatMessage'
     SQL
 
     DB.exec(<<~SQL)
diff --git a/plugins/chat/plugin.rb b/plugins/chat/plugin.rb
index 0766b82cc93..04a5f83a137 100644
--- a/plugins/chat/plugin.rb
+++ b/plugins/chat/plugin.rb
@@ -372,14 +372,6 @@ after_initialize do
     end
   end
 
-  if respond_to?(:register_upload_unused)
-    register_upload_unused do |uploads|
-      uploads.joins("LEFT JOIN chat_uploads cu ON cu.upload_id = uploads.id").where(
-        "cu.upload_id IS NULL",
-      )
-    end
-  end
-
   if respond_to?(:register_upload_in_use)
     register_upload_in_use do |upload|
       ChatMessage.where(
diff --git a/plugins/chat/spec/components/chat_message_creator_spec.rb b/plugins/chat/spec/components/chat_message_creator_spec.rb
index 45f3a4ad2e3..0f6f56a8b97 100644
--- a/plugins/chat/spec/components/chat_message_creator_spec.rb
+++ b/plugins/chat/spec/components/chat_message_creator_spec.rb
@@ -461,7 +461,9 @@ describe Chat::ChatMessageCreator do
             content: "Beep boop",
             upload_ids: [upload1.id],
           )
-        }.to change { ChatUpload.where(upload_id: upload1.id).count }.by(1)
+        }.to not_change { chat_upload_count([upload1]) }.and change {
+                UploadReference.where(upload_id: upload1.id).count
+              }.by(1)
       end
 
       it "can attach multiple uploads to a new message" do
@@ -472,9 +474,9 @@ describe Chat::ChatMessageCreator do
             content: "Beep boop",
             upload_ids: [upload1.id, upload2.id],
           )
-        }.to change { ChatUpload.where(upload_id: upload1.id).count }.by(1).and change {
-                ChatUpload.where(upload_id: upload2.id).count
-              }.by(1)
+        }.to not_change { chat_upload_count([upload1, upload2]) }.and change {
+                UploadReference.where(upload_id: [upload1.id, upload2.id]).count
+              }.by(2)
       end
 
       it "filters out uploads that weren't uploaded by the user" do
@@ -485,7 +487,7 @@ describe Chat::ChatMessageCreator do
             content: "Beep boop",
             upload_ids: [private_upload.id],
           )
-        }.not_to change { ChatUpload.where(upload_id: private_upload.id).count }
+        }.not_to change { chat_upload_count([private_upload]) }
       end
 
       it "doesn't attach uploads when `chat_allow_uploads` is false" do
@@ -497,7 +499,9 @@ describe Chat::ChatMessageCreator do
             content: "Beep boop",
             upload_ids: [upload1.id],
           )
-        }.not_to change { ChatUpload.where(upload_id: upload1.id).count }
+        }.to not_change { chat_upload_count([upload1]) }.and not_change {
+                UploadReference.where(upload_id: upload1.id).count
+              }
       end
     end
   end
@@ -605,4 +609,11 @@ describe Chat::ChatMessageCreator do
       end
     end
   end
+
+  # TODO (martin) Remove this when we remove ChatUpload completely, 2023-04-01
+  def chat_upload_count(uploads)
+    DB.query_single(
+      "SELECT COUNT(*) FROM chat_uploads WHERE upload_id IN (#{uploads.map(&:id).join(",")})",
+    ).first
+  end
 end
diff --git a/plugins/chat/spec/components/chat_message_updater_spec.rb b/plugins/chat/spec/components/chat_message_updater_spec.rb
index f32f979faaf..39c00726bc6 100644
--- a/plugins/chat/spec/components/chat_message_updater_spec.rb
+++ b/plugins/chat/spec/components/chat_message_updater_spec.rb
@@ -329,7 +329,7 @@ describe Chat::ChatMessageUpdater do
           new_content: "I guess this is different",
           upload_ids: [upload2.id, upload1.id],
         )
-      }.not_to change { ChatUpload.count }
+      }.to not_change { chat_upload_count }.and not_change { UploadReference.count }
     end
 
     it "removes uploads that should be removed" do
@@ -340,6 +340,16 @@ describe Chat::ChatMessageUpdater do
           public_chat_channel,
           upload_ids: [upload1.id, upload2.id],
         )
+
+      # TODO (martin) Remove this when we remove ChatUpload completely, 2023-04-01
+      DB.exec(<<~SQL)
+        INSERT INTO chat_uploads(upload_id, chat_message_id, created_at, updated_at)
+        VALUES(#{upload1.id}, #{chat_message.id}, NOW(), NOW())
+      SQL
+      DB.exec(<<~SQL)
+        INSERT INTO chat_uploads(upload_id, chat_message_id, created_at, updated_at)
+        VALUES(#{upload2.id}, #{chat_message.id}, NOW(), NOW())
+      SQL
       expect {
         Chat::ChatMessageUpdater.update(
           guardian: guardian,
@@ -347,7 +357,9 @@ describe Chat::ChatMessageUpdater do
           new_content: "I guess this is different",
           upload_ids: [upload1.id],
         )
-      }.to change { ChatUpload.where(upload_id: upload2.id).count }.by(-1)
+      }.to change { chat_upload_count([upload2]) }.by(-1).and change {
+              UploadReference.where(upload_id: upload2.id).count
+            }.by(-1)
     end
 
     it "removes all uploads if they should be removed" do
@@ -358,6 +370,16 @@ describe Chat::ChatMessageUpdater do
           public_chat_channel,
           upload_ids: [upload1.id, upload2.id],
         )
+
+      # TODO (martin) Remove this when we remove ChatUpload completely, 2023-04-01
+      DB.exec(<<~SQL)
+        INSERT INTO chat_uploads(upload_id, chat_message_id, created_at, updated_at)
+        VALUES(#{upload1.id}, #{chat_message.id}, NOW(), NOW())
+      SQL
+      DB.exec(<<~SQL)
+        INSERT INTO chat_uploads(upload_id, chat_message_id, created_at, updated_at)
+        VALUES(#{upload2.id}, #{chat_message.id}, NOW(), NOW())
+      SQL
       expect {
         Chat::ChatMessageUpdater.update(
           guardian: guardian,
@@ -365,7 +387,9 @@ describe Chat::ChatMessageUpdater do
           new_content: "I guess this is different",
           upload_ids: [],
         )
-      }.to change { ChatUpload.where(chat_message: chat_message).count }.by(-2)
+      }.to change { chat_upload_count([upload1, upload2]) }.by(-2).and change {
+              UploadReference.where(target: chat_message).count
+            }.by(-2)
     end
 
     it "adds one upload if none exist" do
@@ -377,7 +401,9 @@ describe Chat::ChatMessageUpdater do
           new_content: "I guess this is different",
           upload_ids: [upload1.id],
         )
-      }.to change { ChatUpload.where(chat_message: chat_message).count }.by(1)
+      }.to not_change { chat_upload_count([upload1]) }.and change {
+              UploadReference.where(target: chat_message).count
+            }.by(1)
     end
 
     it "adds multiple uploads if none exist" do
@@ -389,7 +415,9 @@ describe Chat::ChatMessageUpdater do
           new_content: "I guess this is different",
           upload_ids: [upload1.id, upload2.id],
         )
-      }.to change { ChatUpload.where(chat_message: chat_message).count }.by(2)
+      }.to not_change { chat_upload_count([upload1, upload2]) }.and change {
+              UploadReference.where(target: chat_message).count
+            }.by(2)
     end
 
     it "doesn't remove existing uploads when upload ids that do not exist are passed in" do
@@ -402,7 +430,9 @@ describe Chat::ChatMessageUpdater do
           new_content: "I guess this is different",
           upload_ids: [0],
         )
-      }.not_to change { ChatUpload.where(chat_message: chat_message).count }
+      }.to not_change { chat_upload_count }.and not_change {
+              UploadReference.where(target: chat_message).count
+            }
     end
 
     it "doesn't add uploads if `chat_allow_uploads` is false" do
@@ -415,7 +445,9 @@ describe Chat::ChatMessageUpdater do
           new_content: "I guess this is different",
           upload_ids: [upload1.id, upload2.id],
         )
-      }.not_to change { ChatUpload.where(chat_message: chat_message).count }
+      }.to not_change { chat_upload_count([upload1, upload2]) }.and not_change {
+              UploadReference.where(target: chat_message).count
+            }
     end
 
     it "doesn't remove existing uploads if `chat_allow_uploads` is false" do
@@ -434,7 +466,9 @@ describe Chat::ChatMessageUpdater do
           new_content: "I guess this is different",
           upload_ids: [],
         )
-      }.not_to change { ChatUpload.where(chat_message: chat_message).count }
+      }.to not_change { chat_upload_count }.and not_change {
+              UploadReference.where(target: chat_message).count
+            }
     end
 
     it "updates if upload is present even if length is less than `chat_minimum_message_length`" do
@@ -553,4 +587,12 @@ describe Chat::ChatMessageUpdater do
       end
     end
   end
+
+  # TODO (martin) Remove this when we remove ChatUpload completely, 2023-04-01
+  def chat_upload_count(uploads = nil)
+    return DB.query_single("SELECT COUNT(*) FROM chat_uploads").first if !uploads
+    DB.query_single(
+      "SELECT COUNT(*) FROM chat_uploads WHERE upload_id IN (#{uploads.map(&:id).join(",")})",
+    ).first
+  end
 end
diff --git a/plugins/chat/spec/jobs/chat_channel_delete_spec.rb b/plugins/chat/spec/jobs/chat_channel_delete_spec.rb
index 033274f04c0..3ab19ae6f3b 100644
--- a/plugins/chat/spec/jobs/chat_channel_delete_spec.rb
+++ b/plugins/chat/spec/jobs/chat_channel_delete_spec.rb
@@ -17,10 +17,15 @@ describe Jobs::ChatChannelDelete do
     10.times { ChatMessageReaction.create(chat_message: messages.sample, user: users.sample) }
 
     10.times do
-      ChatUpload.create(
-        upload: Fabricate(:upload, user: users.sample),
-        chat_message: messages.sample,
-      )
+      upload = Fabricate(:upload, user: users.sample)
+      message = messages.sample
+
+      # TODO (martin) Remove this when we remove ChatUpload completely, 2023-04-01
+      DB.exec(<<~SQL)
+        INSERT INTO chat_uploads(upload_id, chat_message_id, created_at, updated_at)
+        VALUES(#{upload.id}, #{message.id}, NOW(), NOW())
+      SQL
+      UploadReference.create(target: message, upload: upload)
     end
 
     ChatMention.create(
@@ -52,27 +57,45 @@ describe Jobs::ChatChannelDelete do
     chat_channel.trash!
   end
 
+  def counts
+    {
+      incoming_webhooks: IncomingChatWebhook.where(chat_channel_id: chat_channel.id).count,
+      webhook_events:
+        ChatWebhookEvent.where(incoming_chat_webhook_id: @incoming_chat_webhook_id).count,
+      drafts: ChatDraft.where(chat_channel: chat_channel).count,
+      channel_memberships: UserChatChannelMembership.where(chat_channel: chat_channel).count,
+      revisions: ChatMessageRevision.where(chat_message_id: @message_ids).count,
+      mentions: ChatMention.where(chat_message_id: @message_ids).count,
+      chat_uploads:
+        DB.query_single(
+          "SELECT COUNT(*) FROM chat_uploads WHERE chat_message_id IN (#{@message_ids.join(",")})",
+        ).first,
+      upload_references:
+        UploadReference.where(target_id: @message_ids, target_type: "ChatMessage").count,
+      messages: ChatMessage.where(id: @message_ids).count,
+      reactions: ChatMessageReaction.where(chat_message_id: @message_ids).count,
+    }
+  end
+
   it "deletes all of the messages and related records completely" do
-    expect { described_class.new.execute(chat_channel_id: chat_channel.id) }.to change {
-      IncomingChatWebhook.where(chat_channel_id: chat_channel.id).count
-    }.by(-1).and change {
-            ChatWebhookEvent.where(incoming_chat_webhook_id: @incoming_chat_webhook_id).count
-          }.by(-1).and change { ChatDraft.where(chat_channel: chat_channel).count }.by(
-                  -1,
-                ).and change {
-                        UserChatChannelMembership.where(chat_channel: chat_channel).count
-                      }.by(-3).and change {
-                              ChatMessageRevision.where(chat_message_id: @message_ids).count
-                            }.by(-1).and change {
-                                    ChatMention.where(chat_message_id: @message_ids).count
-                                  }.by(-1).and change {
-                                          ChatUpload.where(chat_message_id: @message_ids).count
-                                        }.by(-10).and change {
-                                                ChatMessage.where(id: @message_ids).count
-                                              }.by(-20).and change {
-                                                      ChatMessageReaction.where(
-                                                        chat_message_id: @message_ids,
-                                                      ).count
-                                                    }.by(-10)
+    initial_counts = counts
+    described_class.new.execute(chat_channel_id: chat_channel.id)
+    new_counts = counts
+
+    expect(new_counts[:incoming_webhooks]).to eq(initial_counts[:incoming_webhooks] - 1)
+    expect(new_counts[:webhook_events]).to eq(initial_counts[:webhook_events] - 1)
+    expect(new_counts[:drafts]).to eq(initial_counts[:drafts] - 1)
+    expect(new_counts[:channel_memberships]).to eq(initial_counts[:channel_memberships] - 3)
+    expect(new_counts[:revisions]).to eq(initial_counts[:revisions] - 1)
+    expect(new_counts[:mentions]).to eq(initial_counts[:mentions] - 1)
+    expect(new_counts[:chat_uploads]).to eq(initial_counts[:chat_uploads] - 10)
+    expect(new_counts[:upload_references]).to eq(initial_counts[:upload_references] - 10)
+    expect(new_counts[:messages]).to eq(initial_counts[:messages] - 20)
+    expect(new_counts[:reactions]).to eq(initial_counts[:reactions] - 10)
+  end
+
+  it "does not error if there are no messages in the channel" do
+    other_channel = Fabricate(:chat_channel)
+    expect { described_class.new.execute(chat_channel_id: other_channel.id) }.not_to raise_error
   end
 end
diff --git a/plugins/chat/spec/lib/chat_channel_archive_service_spec.rb b/plugins/chat/spec/lib/chat_channel_archive_service_spec.rb
index d42c0f3d1a9..144b1032257 100644
--- a/plugins/chat/spec/lib/chat_channel_archive_service_spec.rb
+++ b/plugins/chat/spec/lib/chat_channel_archive_service_spec.rb
@@ -152,7 +152,7 @@ describe Chat::ChatChannelArchiveService do
 
       it "successfully links uploads from messages to the post" do
         create_messages(3) && start_archive
-        ChatUpload.create(chat_message: ChatMessage.last, upload: Fabricate(:upload))
+        UploadReference.create(target: ChatMessage.last, upload: Fabricate(:upload))
         subject.new(@channel_archive).execute
         expect(@channel_archive.reload.complete?).to eq(true)
         expect(@channel_archive.destination_topic.posts.last.upload_references.count).to eq(1)
diff --git a/plugins/chat/spec/lib/chat_transcript_service_spec.rb b/plugins/chat/spec/lib/chat_transcript_service_spec.rb
index 0f14d92f016..c9bf1b832e1 100644
--- a/plugins/chat/spec/lib/chat_transcript_service_spec.rb
+++ b/plugins/chat/spec/lib/chat_transcript_service_spec.rb
@@ -130,10 +130,10 @@ describe ChatTranscriptService do
         original_filename: "test_img.jpg",
         extension: "jpg",
       )
-    cu1 = ChatUpload.create(chat_message: message, created_at: 10.seconds.ago, upload: video)
-    cu2 = ChatUpload.create(chat_message: message, created_at: 9.seconds.ago, upload: audio)
-    cu3 = ChatUpload.create(chat_message: message, created_at: 8.seconds.ago, upload: attachment)
-    cu4 = ChatUpload.create(chat_message: message, created_at: 7.seconds.ago, upload: image)
+    UploadReference.create(target: message, created_at: 10.seconds.ago, upload: video)
+    UploadReference.create(target: message, created_at: 9.seconds.ago, upload: audio)
+    UploadReference.create(target: message, created_at: 8.seconds.ago, upload: attachment)
+    UploadReference.create(target: message, created_at: 7.seconds.ago, upload: image)
     video_markdown = UploadMarkdown.new(video).to_markdown
     audio_markdown = UploadMarkdown.new(audio).to_markdown
     attachment_markdown = UploadMarkdown.new(attachment).to_markdown
@@ -166,7 +166,7 @@ describe ChatTranscriptService do
         original_filename: "test_img.jpg",
         extension: "jpg",
       )
-    cu = ChatUpload.create(chat_message: message, created_at: 7.seconds.ago, upload: image)
+    UploadReference.create(target: message, created_at: 7.seconds.ago, upload: image)
     image_markdown = UploadMarkdown.new(image).to_markdown
 
     expect(service(message.id).generate_markdown).to eq(<<~MARKDOWN)
diff --git a/plugins/chat/spec/lib/message_mover_spec.rb b/plugins/chat/spec/lib/message_mover_spec.rb
index 43182c64c1f..6fd4b6079bd 100644
--- a/plugins/chat/spec/lib/message_mover_spec.rb
+++ b/plugins/chat/spec/lib/message_mover_spec.rb
@@ -112,7 +112,7 @@ describe Chat::MessageMover do
 
     it "updates references for reactions, uploads, revisions, mentions, etc." do
       reaction = Fabricate(:chat_message_reaction, chat_message: message1)
-      upload = Fabricate(:chat_upload, chat_message: message1)
+      upload = Fabricate(:upload_reference, target: message1)
       mention = Fabricate(:chat_mention, chat_message: message2, user: acting_user)
       revision = Fabricate(:chat_message_revision, chat_message: message3)
       webhook_event = Fabricate(:chat_webhook_event, chat_message: message3)
@@ -121,7 +121,7 @@ describe Chat::MessageMover do
       moved_messages =
         ChatMessage.where(chat_channel: destination_channel).order("created_at ASC, id ASC").last(3)
       expect(reaction.reload.chat_message_id).to eq(moved_messages.first.id)
-      expect(upload.reload.chat_message_id).to eq(moved_messages.first.id)
+      expect(upload.reload.target_id).to eq(moved_messages.first.id)
       expect(mention.reload.chat_message_id).to eq(moved_messages.second.id)
       expect(revision.reload.chat_message_id).to eq(moved_messages.third.id)
       expect(webhook_event.reload.chat_message_id).to eq(moved_messages.third.id)
diff --git a/plugins/chat/spec/models/chat_message_spec.rb b/plugins/chat/spec/models/chat_message_spec.rb
index 9e305f98f25..c73b1a24315 100644
--- a/plugins/chat/spec/models/chat_message_spec.rb
+++ b/plugins/chat/spec/models/chat_message_spec.rb
@@ -309,7 +309,7 @@ describe ChatMessage do
       gif =
         Fabricate(:upload, original_filename: "cat.gif", width: 400, height: 300, extension: "gif")
       message = Fabricate(:chat_message, message: "")
-      ChatUpload.create(chat_message: message, upload: gif)
+      UploadReference.create(target: message, upload: gif)
 
       expect(message.excerpt).to eq "cat.gif"
     end
@@ -391,8 +391,8 @@ describe ChatMessage do
         )
       image2 =
         Fabricate(:upload, original_filename: "meme.jpg", width: 10, height: 10, extension: "jpg")
-      ChatUpload.create(chat_message: message, upload: image)
-      ChatUpload.create(chat_message: message, upload: image2)
+      UploadReference.create!(target: message, upload: image)
+      UploadReference.create!(target: message, upload: image2)
       expect(message.to_markdown).to eq(<<~MSG.chomp)
       hey friend, what's up?!
 
@@ -479,13 +479,20 @@ describe ChatMessage do
       expect { webhook_1.reload }.to raise_error(ActiveRecord::RecordNotFound)
     end
 
-    it "destroys chat_uploads" do
+    it "destroys upload_references and chat_uploads" do
       message_1 = Fabricate(:chat_message)
-      chat_upload_1 = Fabricate(:chat_upload, chat_message: message_1)
+      upload_reference_1 = Fabricate(:upload_reference, target: message_1)
+      upload_1 = Fabricate(:upload)
+      # TODO (martin) Remove this when we remove ChatUpload completely, 2023-04-01
+      DB.exec(<<~SQL)
+        INSERT INTO chat_uploads(upload_id, chat_message_id, created_at, updated_at)
+        VALUES(#{upload_1.id}, #{message_1.id}, NOW(), NOW())
+      SQL
 
       message_1.destroy!
 
-      expect { chat_upload_1.reload }.to raise_error(ActiveRecord::RecordNotFound)
+      expect(DB.query("SELECT * FROM chat_uploads WHERE upload_id = #{upload_1.id}")).to eq([])
+      expect { upload_reference_1.reload }.to raise_error(ActiveRecord::RecordNotFound)
     end
 
     describe "bookmarks" do
@@ -532,4 +539,39 @@ describe ChatMessage do
       end
     end
   end
+
+  describe "#attach_uploads" do
+    fab!(:chat_message) { Fabricate(:chat_message) }
+    fab!(:upload_1) { Fabricate(:upload) }
+    fab!(:upload_2) { Fabricate(:upload) }
+
+    it "creates an UploadReference record for the provided uploads" do
+      chat_message.attach_uploads([upload_1, upload_2])
+      upload_references = UploadReference.where(upload_id: [upload_1, upload_2])
+      expect(chat_upload_count([upload_1, upload_2])).to eq(0)
+      expect(upload_references.count).to eq(2)
+      expect(upload_references.map(&:target_id).uniq).to eq([chat_message.id])
+      expect(upload_references.map(&:target_type).uniq).to eq(["ChatMessage"])
+    end
+
+    it "does nothing if the message record is new" do
+      expect { ChatMessage.new.attach_uploads([upload_1, upload_2]) }.to not_change {
+        chat_upload_count
+      }.and not_change { UploadReference.count }
+    end
+
+    it "does nothing for an empty uploads array" do
+      expect { chat_message.attach_uploads([]) }.to not_change {
+        chat_upload_count
+      }.and not_change { UploadReference.count }
+    end
+  end
+
+  # TODO (martin) Remove this when we remove ChatUpload completely, 2023-04-01
+  def chat_upload_count(uploads = nil)
+    return DB.query_single("SELECT COUNT(*) FROM chat_uploads").first if !uploads
+    DB.query_single(
+      "SELECT COUNT(*) FROM chat_uploads WHERE upload_id IN (#{uploads.map(&:id).join(",")})",
+    ).first
+  end
 end
diff --git a/plugins/chat/spec/plugin_spec.rb b/plugins/chat/spec/plugin_spec.rb
index 68cdda55f97..431d1ccc616 100644
--- a/plugins/chat/spec/plugin_spec.rb
+++ b/plugins/chat/spec/plugin_spec.rb
@@ -26,7 +26,7 @@ describe Chat do
       )
     end
 
-    it "marks uploads with ChatUpload in use" do
+    it "marks uploads with reference to ChatMessage via UploadReference in use" do
       unused_upload
 
       expect { Jobs::CleanUpUploads.new.execute({}) }.to change { Upload.count }.by(-1)
@@ -61,7 +61,7 @@ describe Chat do
       )
     end
 
-    it "marks uploads with ChatUpload in use" do
+    it "marks uploads with reference to ChatMessage via UploadReference in use" do
       draft_upload
       unused_upload
 
diff --git a/plugins/chat/spec/system/uploads_spec.rb b/plugins/chat/spec/system/uploads_spec.rb
index 6e49290023c..a012d29b86c 100644
--- a/plugins/chat/spec/system/uploads_spec.rb
+++ b/plugins/chat/spec/system/uploads_spec.rb
@@ -79,15 +79,21 @@ describe "Uploading files in chat messages", type: :system, js: true do
 
   context "when editing a message with uploads" do
     fab!(:message_2) { Fabricate(:chat_message, user: current_user, chat_channel: channel_1) }
-    fab!(:chat_upload) { Fabricate(:chat_upload, chat_message: message_2, user: current_user) }
+    fab!(:upload_reference) do
+      Fabricate(
+        :upload_reference,
+        target: message_2,
+        upload: Fabricate(:upload, user: current_user),
+      )
+    end
 
     before do
       channel_1.add(current_user)
       sign_in(current_user)
 
       file = file_from_fixtures("logo-dev.png", "images")
-      url = Discourse.store.store_upload(file, chat_upload.upload)
-      chat_upload.upload.update!(url: url, sha1: Upload.generate_digest(file))
+      url = Discourse.store.store_upload(file, upload_reference.upload)
+      upload_reference.upload.update!(url: url, sha1: Upload.generate_digest(file))
     end
 
     it "allows deleting uploads" do
diff --git a/spec/fabricators/upload_fabricator.rb b/spec/fabricators/upload_fabricator.rb
index aec9a20721d..3101a110b27 100644
--- a/spec/fabricators/upload_fabricator.rb
+++ b/spec/fabricators/upload_fabricator.rb
@@ -97,3 +97,8 @@ Fabricator(:secure_upload_s3, from: :upload_s3) do
   sha1 { SecureRandom.hex(20) }
   original_sha1 { sequence(:sha1) { |n| Digest::SHA1.hexdigest(n.to_s) } }
 end
+
+Fabricator(:upload_reference) do
+  target
+  upload
+end