diff --git a/app/javascript/dashboard/components-next/captain/assistant/AddNewScenariosDialog.vue b/app/javascript/dashboard/components-next/captain/assistant/AddNewScenariosDialog.vue
index 89f115a64..08d79d27c 100644
--- a/app/javascript/dashboard/components-next/captain/assistant/AddNewScenariosDialog.vue
+++ b/app/javascript/dashboard/components-next/captain/assistant/AddNewScenariosDialog.vue
@@ -107,6 +107,7 @@ const onClickCancel = () => {
 
         <TextArea
           v-model="state.description"
+          :max-length="500"
           :label="
             t('CAPTAIN.ASSISTANTS.SCENARIOS.ADD.NEW.FORM.DESCRIPTION.LABEL')
           "
diff --git a/app/javascript/dashboard/components-next/captain/assistant/ScenariosCard.vue b/app/javascript/dashboard/components-next/captain/assistant/ScenariosCard.vue
index d891c193a..d3c18e79d 100644
--- a/app/javascript/dashboard/components-next/captain/assistant/ScenariosCard.vue
+++ b/app/javascript/dashboard/components-next/captain/assistant/ScenariosCard.vue
@@ -213,6 +213,7 @@ const renderInstruction = instruction => () =>
 
       <TextArea
         v-model="state.description"
+        :max-length="500"
         :label="
           t('CAPTAIN.ASSISTANTS.SCENARIOS.ADD.NEW.FORM.DESCRIPTION.LABEL')
         "
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/assistant/AssistantForm.vue b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/AssistantForm.vue
index 363b9624c..1baa60586 100644
--- a/app/javascript/dashboard/components-next/captain/pageComponents/assistant/AssistantForm.vue
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/AssistantForm.vue
@@ -122,6 +122,7 @@ watch(
 
     <Editor
       v-model="state.description"
+      :max-length="500"
       :label="t('CAPTAIN.ASSISTANTS.FORM.DESCRIPTION.LABEL')"
       :placeholder="t('CAPTAIN.ASSISTANTS.FORM.DESCRIPTION.PLACEHOLDER')"
       :message="formErrors.description"
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantBasicSettingsForm.vue b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantBasicSettingsForm.vue
index af80b7489..31a67c7b8 100644
--- a/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantBasicSettingsForm.vue
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/assistant/settings/AssistantBasicSettingsForm.vue
@@ -117,6 +117,7 @@ watch(
 
     <Editor
       v-model="state.description"
+      :max-length="500"
       :label="t('CAPTAIN.ASSISTANTS.FORM.DESCRIPTION.LABEL')"
       :placeholder="t('CAPTAIN.ASSISTANTS.FORM.DESCRIPTION.PLACEHOLDER')"
       :message="formErrors.description"
diff --git a/db/migrate/20260710000000_change_captain_assistant_description_to_text.rb b/db/migrate/20260710000000_change_captain_assistant_description_to_text.rb
new file mode 100644
index 000000000..4d68ddc3a
--- /dev/null
+++ b/db/migrate/20260710000000_change_captain_assistant_description_to_text.rb
@@ -0,0 +1,9 @@
+class ChangeCaptainAssistantDescriptionToText < ActiveRecord::Migration[7.0]
+  def up
+    change_column :captain_assistants, :description, :text
+  end
+
+  def down
+    change_column :captain_assistants, :description, :string
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 5e506a475..d5f975f16 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.1].define(version: 2026_07_06_215758) do
+ActiveRecord::Schema[7.1].define(version: 2026_07_10_000000) do
   # These extensions should be enabled to support this database
   enable_extension "pg_stat_statements"
   enable_extension "pg_trgm"
@@ -343,7 +343,7 @@ ActiveRecord::Schema[7.1].define(version: 2026_07_06_215758) do
   create_table "captain_assistants", force: :cascade do |t|
     t.string "name", null: false
     t.bigint "account_id", null: false
-    t.string "description"
+    t.text "description"
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
     t.jsonb "config", default: {}, null: false
diff --git a/enterprise/app/models/captain/assistant.rb b/enterprise/app/models/captain/assistant.rb
index 0735987de..d3f6cda8a 100644
--- a/enterprise/app/models/captain/assistant.rb
+++ b/enterprise/app/models/captain/assistant.rb
@@ -4,7 +4,7 @@
 #
 #  id                  :bigint           not null, primary key
 #  config              :jsonb            not null
-#  description         :string
+#  description         :text
 #  guardrails          :jsonb
 #  name                :string           not null
 #  response_guidelines :jsonb
@@ -17,6 +17,8 @@
 #  index_captain_assistants_on_account_id  (account_id)
 #
 class Captain::Assistant < ApplicationRecord
+  DESCRIPTION_LENGTH_LIMIT = 500
+
   include Avatarable
   include Concerns::CaptainToolsHelpers
   include Concerns::Agentable
@@ -39,7 +41,7 @@ class Captain::Assistant < ApplicationRecord
   store_accessor :config, :temperature, :feature_faq, :feature_memory, :feature_contact_attributes, :product_name
 
   validates :name, presence: true
-  validates :description, presence: true
+  validates :description, presence: true, length: { maximum: DESCRIPTION_LENGTH_LIMIT }
   validates :account_id, presence: true
 
   scope :ordered, -> { order(created_at: :desc) }
diff --git a/enterprise/app/models/captain/scenario.rb b/enterprise/app/models/captain/scenario.rb
index 8a6a3c979..895133897 100644
--- a/enterprise/app/models/captain/scenario.rb
+++ b/enterprise/app/models/captain/scenario.rb
@@ -21,6 +21,8 @@
 #  index_captain_scenarios_on_enabled                   (enabled)
 #
 class Captain::Scenario < ApplicationRecord
+  DESCRIPTION_LENGTH_LIMIT = 500
+
   include Concerns::CaptainToolsHelpers
   include Concerns::Agentable
 
@@ -43,7 +45,7 @@ class Captain::Scenario < ApplicationRecord
   belongs_to :account
 
   validates :title, presence: true
-  validates :description, presence: true
+  validates :description, presence: true, length: { maximum: DESCRIPTION_LENGTH_LIMIT }
   validates :instruction, presence: true
   validates :assistant_id, presence: true
   validates :account_id, presence: true
diff --git a/enterprise/app/services/captain/onboarding/website_analyzer_service.rb b/enterprise/app/services/captain/onboarding/website_analyzer_service.rb
index fb6bab33b..10aa4e4ce 100644
--- a/enterprise/app/services/captain/onboarding/website_analyzer_service.rb
+++ b/enterprise/app/services/captain/onboarding/website_analyzer_service.rb
@@ -97,7 +97,7 @@ class Captain::Onboarding::WebsiteAnalyzerService < Llm::BaseAiService
       Guidelines:
       - business_name: Extract the actual company/brand name from the content
       - suggested_assistant_name: Create a friendly, professional name that customers would want to interact with
-      - description: Provide context about the business and what the assistant can help with. Keep it general and adaptable rather than overly specific. For example: "You specialize in helping customers with their orders and product questions" or "You assist customers with their account needs and general inquiries"
+      - description: Provide context about the business and what the assistant can help with in no more than 500 characters. Keep it general and adaptable rather than overly specific. For example: "You specialize in helping customers with their orders and product questions" or "You assist customers with their account needs and general inquiries"
 
       Website content:
       #{@website_content}