diff --git a/TOOLS.md b/TOOLS.md
index 73a2758..7f82f01 100644
--- a/TOOLS.md
+++ b/TOOLS.md
@@ -1,21 +1,25 @@
 # Available Iterable MCP Tools (104 tools)
 
-**Legend:** 🔒 = Contains PII, ✏️ = Write operation
+**Legend:**
+- 🔒 = Requires enabling user PII access
+- ✏️ = Requires enabling writes
+- ✉️ = Requires enabling sends
+
 
 ## Campaigns (13 tools)
 - **abort_campaign** ✏️: Abort a campaign that is currently running
-- **activate_triggered_campaign** ✏️: Activate a triggered campaign (requires API triggered campaign activation enabled)
+- **activate_triggered_campaign** ✏️✉️: Activate a triggered campaign (requires API triggered campaign activation enabled)
 - **archive_campaigns** ✏️: Archive one or more campaigns. Scheduled/recurring campaigns will be cancelled, running campaigns will be aborted.
 - **cancel_campaign** ✏️: Cancel a scheduled or recurring campaign
-- **create_campaign** ✏️: Create a new blast or triggered campaign from an existing template. If listIds are provided, the campaign will be a blast campaign, otherwise it will be a triggered campaign. Blast campaigns will be sent immediately if sendAt is not provided.
+- **create_campaign** ✏️✉️: Create a new blast or triggered campaign from an existing template. If listIds are provided, the campaign will be a blast campaign, otherwise it will be a triggered campaign. Blast campaigns will be sent immediately if sendAt is not provided.
 - **deactivate_triggered_campaign** ✏️: Deactivate a triggered campaign (requires API triggered campaign deactivation enabled)
 - **get_campaign**: Get detailed information about a specific campaign
 - **get_campaign_metrics**: Get campaign performance metrics
 - **get_campaigns**: Retrieve campaigns
 - **get_child_campaigns**: Get child campaigns generated by a recurring campaign
-- **schedule_campaign** ✏️: Schedule an existing campaign to be sent at a specific time
-- **send_campaign** ✏️: Send an existing scheduled campaign immediately
-- **trigger_campaign** ✏️: Trigger a campaign to send to specified lists
+- **schedule_campaign** ✏️✉️: Schedule an existing campaign to be sent at a specific time
+- **send_campaign** ✏️✉️: Send an existing scheduled campaign immediately
+- **trigger_campaign** ✏️✉️: Trigger a campaign to send to specified lists
 
 ## Catalogs (12 tools)
 - **bulk_delete_catalog_items** ✏️: Bulk delete catalog items by their IDs
@@ -41,15 +45,15 @@
 ## Events (4 tools)
 - **get_user_events_by_email** 🔒: Get event history for a user by email address
 - **get_user_events_by_user_id** 🔒: Get event history for a user by user ID
-- **track_bulk_events** 🔒✏️: Track multiple events in a single request for better performance
-- **track_event** 🔒✏️: Track a custom event for a user
+- **track_bulk_events** 🔒✏️✉️: Track multiple events in a single request for better performance
+- **track_event** 🔒✏️✉️: Track a custom event for a user
 
 ## Experiments (1 tools)
 - **get_experiment_metrics**: Get experiment metrics for A/B testing analysis (currently supports email experiments only)
 
 ## Journeys (2 tools)
 - **get_journeys**: Get journeys (workflows) with optional pagination and state filtering
-- **trigger_journey** 🔒✏️: Trigger a journey (workflow) for a user
+- **trigger_journey** 🔒✏️✉️: Trigger a journey (workflow) for a user
 
 ## Lists (8 tools)
 - **create_list** ✏️: Create a new user list
@@ -72,12 +76,12 @@
 - **get_embedded_messages** 🔒: Get embedded messages for a user, grouped by placement ID
 - **get_in_app_messages** 🔒: Get in-app messages for a user
 - **get_message_types**: Get all message types within the project for use in templates
-- **send_email** 🔒✏️: Send email to user
-- **send_in_app** 🔒✏️: Send in-app message to user
-- **send_push** 🔒✏️: Send push notification to user
-- **send_sms** 🔒✏️: Send SMS message to user
-- **send_web_push** 🔒✏️: Send web push notification to user
-- **send_whatsapp** 🔒✏️: Send WhatsApp message to user
+- **send_email** 🔒✏️✉️: Send email to user
+- **send_in_app** 🔒✏️✉️: Send in-app message to user
+- **send_push** 🔒✏️✉️: Send push notification to user
+- **send_sms** 🔒✏️✉️: Send SMS message to user
+- **send_web_push** 🔒✏️✉️: Send web push notification to user
+- **send_whatsapp** 🔒✏️✉️: Send WhatsApp message to user
 
 ## Snippets (5 tools)
 - **create_snippet** ✏️: Create a new snippet with Handlebars templating support
@@ -103,10 +107,10 @@
 - **get_templates**: Retrieve templates
 - **preview_email_template**: Preview email template with custom data. Returns fully rendered HTML with user, event, and/or data feed data substituted.
 - **preview_inapp_template**: Preview in-app message template with custom data. Returns fully rendered HTML with user, event, and/or data feed data substituted.
-- **send_email_template_proof** 🔒✏️: Send a proof of a email template to a specific user
-- **send_inapp_template_proof** 🔒✏️: Send a proof of a in-app message template to a specific user
-- **send_push_template_proof** 🔒✏️: Send a proof of a push notification template to a specific user
-- **send_sms_template_proof** 🔒✏️: Send a proof of a SMS template to a specific user
+- **send_email_template_proof** 🔒✏️✉️: Send a proof of a email template to a specific user
+- **send_inapp_template_proof** 🔒✏️✉️: Send a proof of a in-app message template to a specific user
+- **send_push_template_proof** 🔒✏️✉️: Send a proof of a push notification template to a specific user
+- **send_sms_template_proof** 🔒✏️✉️: Send a proof of a SMS template to a specific user
 - **update_email_template** ✏️: Update existing email template by templateId
 - **update_inapp_template** ✏️: Update existing in-app message template by templateId
 - **update_push_template** ✏️: Update existing push notification template by templateId
diff --git a/scripts/update-tools.js b/scripts/update-tools.js
index 788a7d8..6a2f6ca 100644
--- a/scripts/update-tools.js
+++ b/scripts/update-tools.js
@@ -1,6 +1,10 @@
 import { readFileSync, writeFileSync } from "fs";
 import { TOOL_CREATORS_BY_CATEGORY } from "../dist/tools/index.js";
-import { NON_PII_TOOLS, READ_ONLY_TOOLS } from "../dist/tool-filter.js";
+import {
+  NON_PII_TOOLS,
+  READ_ONLY_TOOLS,
+  SEND_TOOLS,
+} from "../dist/tool-filter.js";
 
 const TOOLS_FILE = "TOOLS.md";
 
@@ -20,6 +24,7 @@ try {
     let icons = "";
     if (!NON_PII_TOOLS.has(toolName)) icons += "🔒";
     if (!READ_ONLY_TOOLS.has(toolName)) icons += "✏️";
+    if (SEND_TOOLS.has(toolName)) icons += "✉️";
     return icons ? ` ${icons}` : "";
   };
 
@@ -27,7 +32,11 @@ try {
     [
       `# Available Iterable MCP Tools (${totalToolCount} tools)`,
       ``,
-      `**Legend:** 🔒 = Contains PII, ✏️ = Write operation`,
+      `**Legend:**`,
+      `- 🔒 = Requires enabling user PII access`,
+      `- ✏️ = Requires enabling writes`,
+      `- ✉️ = Requires enabling sends`,
+      ``,
       ...toolsByCategory.flatMap(({ category, tools }) => [
         `\n## ${category} (${tools.length} tools)`,
         ...tools.map(