diff --git a/plugins/chat/app/controllers/chat_controller.rb b/plugins/chat/app/controllers/chat_controller.rb
index 9849ffc2909..31ad38e02a6 100644
--- a/plugins/chat/app/controllers/chat_controller.rb
+++ b/plugins/chat/app/controllers/chat_controller.rb
@@ -432,9 +432,10 @@ class Chat::ChatController < Chat::ChatBaseController
 
   def set_draft
     if params[:data].present?
-      ChatDraft.find_or_initialize_by(user: current_user, chat_channel_id: @chat_channel.id).update(
-        data: params[:data],
-      )
+      ChatDraft.find_or_initialize_by(
+        user: current_user,
+        chat_channel_id: @chat_channel.id,
+      ).update!(data: params[:data])
     else
       ChatDraft.where(user: current_user, chat_channel_id: @chat_channel.id).destroy_all
     end
diff --git a/plugins/chat/app/models/chat_draft.rb b/plugins/chat/app/models/chat_draft.rb
index 1d3781fa826..7dc1b7feeb0 100644
--- a/plugins/chat/app/models/chat_draft.rb
+++ b/plugins/chat/app/models/chat_draft.rb
@@ -3,6 +3,13 @@
 class ChatDraft < ActiveRecord::Base
   belongs_to :user
   belongs_to :chat_channel
+
+  validate :data_length
+  def data_length
+    if self.data && self.data.length > SiteSetting.max_chat_draft_length
+      self.errors.add(:base, I18n.t("chat.errors.draft_too_long"))
+    end
+  end
 end
 
 # == Schema Information
diff --git a/plugins/chat/assets/javascripts/discourse/services/chat.js b/plugins/chat/assets/javascripts/discourse/services/chat.js
index 0cb1c56ace3..931f480e438 100644
--- a/plugins/chat/assets/javascripts/discourse/services/chat.js
+++ b/plugins/chat/assets/javascripts/discourse/services/chat.js
@@ -373,11 +373,13 @@ export default class Chat extends Service {
       data.data = JSON.stringify(draft);
     }
 
-    ajax("/chat/drafts", { type: "POST", data, ignoreUnsent: false })
+    ajax("/chat/drafts.json", { type: "POST", data, ignoreUnsent: false })
       .then(() => {
         this.markNetworkAsReliable();
       })
       .catch((error) => {
+        // we ignore a draft which can't be saved because it's too big
+        // and only deal with network error for now
         if (!error.jqXHR?.responseJSON?.errors?.length) {
           this.markNetworkAsUnreliable();
         }
diff --git a/plugins/chat/config/locales/server.en.yml b/plugins/chat/config/locales/server.en.yml
index f0c8abefb9d..372eda5e4a3 100644
--- a/plugins/chat/config/locales/server.en.yml
+++ b/plugins/chat/config/locales/server.en.yml
@@ -59,6 +59,7 @@ en:
       delete_channel_failed: "Delete channel failed, please try again."
       minimum_length_not_met: "Message is too short, must have a minimum of %{minimum} characters."
       message_too_long: "Message is too long, messages must be a maximum of %{maximum} characters."
+      draft_too_long: "Draft is too long."
       max_reactions_limit_reached: "New reactions are not allowed on this message."
       message_move_invalid_channel: "The source and destination channel must be public channels."
       message_move_no_messages_found: "No messages were found with the provided message IDs."
diff --git a/plugins/chat/config/settings.yml b/plugins/chat/config/settings.yml
index 072e9d97921..015477dc038 100644
--- a/plugins/chat/config/settings.yml
+++ b/plugins/chat/config/settings.yml
@@ -110,3 +110,6 @@ chat:
     default: 5
     max: 10
     min: 0
+  max_chat_draft_length:
+    default: 50_000
+    hidden: true
diff --git a/plugins/chat/db/post_migrate/20230116090324_drop_chat_drafts_over_max_length.rb b/plugins/chat/db/post_migrate/20230116090324_drop_chat_drafts_over_max_length.rb
new file mode 100644
index 00000000000..1d6913086f5
--- /dev/null
+++ b/plugins/chat/db/post_migrate/20230116090324_drop_chat_drafts_over_max_length.rb
@@ -0,0 +1,17 @@
+# frozen_string_literal: true
+
+class DropChatDraftsOverMaxLength < ActiveRecord::Migration[7.0]
+  def up
+    if table_exists?(:chat_drafts)
+      # Delete abusive drafts
+      execute <<~SQL
+        DELETE FROM chat_drafts
+        WHERE LENGTH(data) > 50000
+      SQL
+    end
+  end
+
+  def down
+    raise ActiveRecord::IrreversibleMigration
+  end
+end
diff --git a/plugins/chat/plugin.rb b/plugins/chat/plugin.rb
index b3b5070a198..8a9127e51e6 100644
--- a/plugins/chat/plugin.rb
+++ b/plugins/chat/plugin.rb
@@ -455,6 +455,8 @@ after_initialize do
   add_to_serializer(:current_user, :chat_drafts) do
     ChatDraft
       .where(user_id: object.id)
+      .order(updated_at: :desc)
+      .limit(20)
       .pluck(:chat_channel_id, :data)
       .map { |row| { channel_id: row[0], data: row[1] } }
   end
diff --git a/plugins/chat/spec/fabricators/chat_fabricator.rb b/plugins/chat/spec/fabricators/chat_fabricator.rb
index e123c06bc54..a8d7f3e544e 100644
--- a/plugins/chat/spec/fabricators/chat_fabricator.rb
+++ b/plugins/chat/spec/fabricators/chat_fabricator.rb
@@ -126,3 +126,16 @@ Fabricator(:user_chat_channel_membership_for_dm, from: :user_chat_channel_member
   desktop_notification_level 2
   mobile_notification_level 2
 end
+
+Fabricator(:chat_draft) do
+  user
+  chat_channel
+
+  transient :value, "chat draft message"
+  transient :uploads, []
+  transient :reply_to_msg
+
+  data do |attrs|
+    { value: attrs[:value], replyToMsg: attrs[:reply_to_msg], uploads: attrs[:uploads] }.to_json
+  end
+end
diff --git a/plugins/chat/spec/models/chat_draft_spec.rb b/plugins/chat/spec/models/chat_draft_spec.rb
new file mode 100644
index 00000000000..27794bafaec
--- /dev/null
+++ b/plugins/chat/spec/models/chat_draft_spec.rb
@@ -0,0 +1,18 @@
+# frozen_string_literal: true
+
+RSpec.describe ChatDraft do
+  before { SiteSetting.max_chat_draft_length = 100 }
+
+  it "errors when data.value is greater than `max_chat_draft_length`" do
+    draft =
+      described_class.create(
+        user_id: Fabricate(:user).id,
+        chat_channel_id: Fabricate(:chat_channel).id,
+        data: { value: "A" * (SiteSetting.max_chat_draft_length + 1) }.to_json,
+      )
+
+    expect(draft.errors.full_messages).to eq(
+      [I18n.t("chat.errors.draft_too_long", { maximum: SiteSetting.max_chat_draft_length })],
+    )
+  end
+end
diff --git a/plugins/chat/spec/requests/chat_controller_spec.rb b/plugins/chat/spec/requests/chat_controller_spec.rb
index 8ff5912df5b..c2eac575378 100644
--- a/plugins/chat/spec/requests/chat_controller_spec.rb
+++ b/plugins/chat/spec/requests/chat_controller_spec.rb
@@ -1285,6 +1285,19 @@ RSpec.describe Chat::ChatController do
         post "/chat/drafts.json", params: { chat_channel_id: dm_channel.id, data: "{}" }
       }.to change { ChatDraft.count }.by(1)
     end
+
+    it "cannot create a too long chat draft" do
+      SiteSetting.max_chat_draft_length = 100
+
+      post "/chat/drafts.json",
+           params: {
+             chat_channel_id: chat_channel.id,
+             data: { value: "a" * (SiteSetting.max_chat_draft_length + 1) }.to_json,
+           }
+
+      expect(response.status).to eq(422)
+      expect(response.parsed_body["errors"]).to eq([I18n.t("chat.errors.draft_too_long")])
+    end
   end
 
   describe "#message_link" do
diff --git a/plugins/chat/spec/serializer/core_ext/current_user_serializer_spec.rb b/plugins/chat/spec/serializer/core_ext/current_user_serializer_spec.rb
new file mode 100644
index 00000000000..2e2fd20a0ef
--- /dev/null
+++ b/plugins/chat/spec/serializer/core_ext/current_user_serializer_spec.rb
@@ -0,0 +1,40 @@
+# frozen_string_literal: true
+
+RSpec.describe CurrentUserSerializer do
+  fab!(:current_user) { Fabricate(:user) }
+
+  let(:serializer) do
+    described_class.new(current_user, scope: Guardian.new(current_user), root: false)
+  end
+
+  before do
+    SiteSetting.chat_enabled = true
+    SiteSetting.chat_allowed_groups = Group::AUTO_GROUPS[:everyone]
+    current_user.user_option.update(chat_enabled: true)
+  end
+
+  describe "#chat_drafts" do
+    context "when user can't chat" do
+      before { SiteSetting.chat_allowed_groups = Group::AUTO_GROUPS[:staff] }
+
+      it "is not present" do
+        expect(serializer.as_json[:chat_drafts]).to be_blank
+      end
+    end
+
+    it "is ordered by most recent drafts" do
+      Fabricate(:chat_draft, user: current_user, value: "second draft")
+      Fabricate(:chat_draft, user: current_user, value: "first draft")
+
+      values =
+        serializer.as_json[:chat_drafts].map { |draft| MultiJson.load(draft[:data])["value"] }
+      expect(values).to eq(["first draft", "second draft"])
+    end
+
+    it "limits the numbers of drafts" do
+      21.times { Fabricate(:chat_draft, user: current_user) }
+
+      expect(serializer.as_json[:chat_drafts].length).to eq(20)
+    end
+  end
+end