diff --git a/internal/assignment/crm_assignment.go b/internal/assignment/crm_assignment.go
index ac7f761..0ae98c3 100644
--- a/internal/assignment/crm_assignment.go
+++ b/internal/assignment/crm_assignment.go
@@ -65,6 +65,11 @@ func AssignCRMMiler(bookingID int) {
 		"booking_id", bookingID,
 		"max_retries", maxRetries,
 	)
+
+	// Terminal failure — same handoff as the B2C path. Both entry points must
+	// publish, or failures arriving via the CRM console stay invisible to the
+	// DispatchAgent.
+	publishAssignmentFailed(bookingID, reasonNoMilerAvailable)
 }
 
 // tryAssign performs a single attempt: queries Redis GEO, scores candidates, commits.
diff --git a/internal/assignment/customer_assignment.go b/internal/assignment/customer_assignment.go
index 1c0e72b..f8030ee 100644
--- a/internal/assignment/customer_assignment.go
+++ b/internal/assignment/customer_assignment.go
@@ -58,6 +58,11 @@ func AssignCustomerMiler(bookingID int) {
 		"booking_id", bookingID,
 		"max_retries", maxRetries,
 	)
+
+	// Terminal failure — hand off to the AI layer's DispatchAgent, which owns
+	// what happens next (coverage sweep, escalation). Reached only after every
+	// retry is exhausted, so it fires at most once per booking.
+	publishAssignmentFailed(bookingID, reasonNoMilerAvailable)
 }
 
 // tryCustomerAssign performs one full attempt: GEO miler search → provider selection → commit.
diff --git a/internal/assignment/failure_event.go b/internal/assignment/failure_event.go
new file mode 100644
index 0000000..e74dc42
--- /dev/null
+++ b/internal/assignment/failure_event.go
@@ -0,0 +1,79 @@
+package assignment
+
+import (
+	"encoding/json"
+	"time"
+
+	"doormile/db"
+	"doormile/models"
+	"doormile/utils"
+)
+
+// assignmentFailedSubject is the JetStream subject the AI layer's DispatchAgent
+// binds its durable consumer to. It must be present on the ASSIGNMENTS stream
+// before anything publishes here — JetStream drops messages on subjects the
+// stream does not cover, silently and with a successful-looking publish.
+const assignmentFailedSubject = "booking.assignment_failed"
+
+// Reasons carried on the failure event. Kept coarse on purpose: the consumer
+// branches on booking_id and coordinates, and treats reason as diagnostic only.
+const (
+	reasonNoMilerAvailable = "NO_MILER_AVAILABLE"
+)
+
+// publishAssignmentFailed emits booking.assignment_failed after auto-assignment
+// has genuinely given up on a booking.
+//
+// Call this only from the terminal branch of an assignment entry point — after
+// every retry is exhausted — never from inside a single attempt. The per-attempt
+// paths (no eligible candidates, decision-engine escalation) fire up to
+// maxRetries times for a booking that may still succeed on a later attempt, and
+// publishing there would report failures that never happened.
+//
+// Mirrors publishAssignment/publishCustomerAssignment: non-fatal, so a NATS
+// outage degrades to a log line rather than breaking the assignment goroutine.
+func publishAssignmentFailed(bookingID int, reason string) {
+	if db.Js == nil {
+		return
+	}
+
+	payload := map[string]interface{}{
+		"booking_id": bookingID,
+		"reason":     reason,
+		"failed_at":  time.Now().UnixMilli(),
+	}
+
+	// Pickup coordinates drive the consumer's coverage sweep. They aren't in
+	// scope at the call site, so re-read the booking — one indexed lookup on a
+	// path that only runs after retries have already been exhausted. If the
+	// read fails we still publish: the consumer treats missing coordinates as
+	// "skip the sweep" and degrades safely rather than losing the event.
+	var booking models.PickupBooking
+	if err := db.DB.Select("pickuplatitude", "pickuplongitude", "bookingno").
+		First(&booking, bookingID).Error; err != nil {
+		utils.Warn("Assignment: could not load booking for failure event; publishing without coordinates",
+			"booking_id", bookingID, "error", err)
+	} else {
+		payload["booking_no"] = booking.Bookingno
+		if booking.Pickuplatitude != 0 || booking.Pickuplongitude != 0 {
+			payload["lat"] = booking.Pickuplatitude
+			payload["lon"] = booking.Pickuplongitude
+		}
+	}
+
+	data, err := json.Marshal(payload)
+	if err != nil {
+		utils.Warn("Assignment: failed to marshal assignment-failed payload",
+			"booking_id", bookingID, "error", err)
+		return
+	}
+
+	if _, err := db.Js.Publish(assignmentFailedSubject, data); err != nil {
+		utils.Warn("Assignment: NATS publish failed for assignment-failed event",
+			"booking_id", bookingID, "error", err)
+		return
+	}
+
+	utils.Info("Assignment: published "+assignmentFailedSubject,
+		"booking_id", bookingID, "reason", reason)
+}