diff --git a/src/app/api/whatsapp/webhook/route.ts b/src/app/api/whatsapp/webhook/route.ts
index f0569fa..13a3181 100644
--- a/src/app/api/whatsapp/webhook/route.ts
+++ b/src/app/api/whatsapp/webhook/route.ts
@@ -383,6 +383,17 @@ async function processMessage(
       ? 'image'   // stickers are images
       : 'text'    // reaction, unknown → text fallback
 
+  // Determine whether this is the contact's very first inbound message
+  // BEFORE we insert, so the count is accurate. Covers the case where
+  // the contact row already exists (manual add / CSV import) but they've
+  // never messaged us before — which new_contact_created wouldn't catch.
+  const { count: priorCustomerMsgCount } = await supabaseAdmin()
+    .from('messages')
+    .select('id', { count: 'exact', head: true })
+    .eq('conversation_id', conversation.id)
+    .eq('sender_type', 'customer')
+  const isFirstInboundMessage = (priorCustomerMsgCount ?? 0) === 0
+
   const { error: msgError } = await supabaseAdmin().from('messages').insert({
     conversation_id: conversation.id,
     sender_type: 'customer',
@@ -425,10 +436,20 @@ async function processMessage(
   // Fire-and-forget: a slow or failing automation must not block the
   // webhook's 200 OK response to Meta.
   const inboundText = contentText ?? message.text?.body ?? ''
-  const automationTriggers: ('new_contact_created' | 'new_message_received' | 'keyword_match')[] =
-    contactOutcome.wasCreated
-      ? ['new_contact_created', 'new_message_received', 'keyword_match']
-      : ['new_message_received', 'keyword_match']
+  const automationTriggers: (
+    | 'new_contact_created'
+    | 'first_inbound_message'
+    | 'new_message_received'
+    | 'keyword_match'
+  )[] = ['new_message_received', 'keyword_match']
+  // new_contact_created fires only when the webhook just auto-created the
+  // contact row. first_inbound_message fires whenever this is the contact's
+  // first-ever customer-sent message — a superset that also catches
+  // manually-imported contacts sending for the first time. We dispatch both
+  // so users can pick whichever semantic they want; an automation that
+  // listens to only one trigger runs only when that trigger matches.
+  if (contactOutcome.wasCreated) automationTriggers.unshift('new_contact_created')
+  if (isFirstInboundMessage) automationTriggers.unshift('first_inbound_message')
   for (const triggerType of automationTriggers) {
     runAutomationsForTrigger({
       userId,
diff --git a/src/components/automations/automation-builder.tsx b/src/components/automations/automation-builder.tsx
index 7371e01..04d3a08 100644
--- a/src/components/automations/automation-builder.tsx
+++ b/src/components/automations/automation-builder.tsx
@@ -106,8 +106,13 @@ const ADDABLE_STEPS: AutomationStepType[] = [
 
 const TRIGGER_OPTIONS: { value: AutomationTriggerType; label: string; hint: string }[] = [
   { value: "new_message_received", label: "New Message Received", hint: "Any incoming message" },
+  {
+    value: "first_inbound_message",
+    label: "First Message from Contact",
+    hint: "First time this contact ever messages you (works for manually-added contacts too)",
+  },
   { value: "keyword_match", label: "Keyword Match", hint: "Message contains specific keyword(s)" },
-  { value: "new_contact_created", label: "New Contact Created", hint: "When a contact is auto-created" },
+  { value: "new_contact_created", label: "New Contact Created", hint: "When a contact is auto-created from an incoming message" },
   { value: "conversation_assigned", label: "Conversation Assigned", hint: "When assigned to an agent" },
   { value: "tag_added", label: "Tag Added", hint: "When a tag is added to a contact" },
   { value: "time_based", label: "Time-Based", hint: "On a recurring schedule" },
diff --git a/src/lib/automations/trigger-meta.ts b/src/lib/automations/trigger-meta.ts
index 2b05466..b733dd4 100644
--- a/src/lib/automations/trigger-meta.ts
+++ b/src/lib/automations/trigger-meta.ts
@@ -11,6 +11,10 @@ export const TRIGGER_META: Record<AutomationTriggerType, TriggerMeta> = {
     label: 'New Message',
     pillClass: 'border-blue-500/30 bg-blue-500/10 text-blue-300',
   },
+  first_inbound_message: {
+    label: 'First Message from Contact',
+    pillClass: 'border-teal-500/30 bg-teal-500/10 text-teal-300',
+  },
   keyword_match: {
     label: 'Keyword Match',
     pillClass: 'border-purple-500/30 bg-purple-500/10 text-purple-300',
diff --git a/src/types/index.ts b/src/types/index.ts
index e60c9b9..30a688d 100644
--- a/src/types/index.ts
+++ b/src/types/index.ts
@@ -214,6 +214,7 @@ export interface BroadcastRecipient {
 
 export type AutomationTriggerType =
   | 'new_message_received'
+  | 'first_inbound_message'
   | 'keyword_match'
   | 'new_contact_created'
   | 'conversation_assigned'