diff --git a/@packages/imessage/Sources/IMessageSync/Sender.swift b/@packages/imessage/Sources/IMessageSync/Sender.swift
index 8da4736..4083f13 100644
--- a/@packages/imessage/Sources/IMessageSync/Sender.swift
+++ b/@packages/imessage/Sources/IMessageSync/Sender.swift
@@ -88,9 +88,23 @@ class SendService {
             .replacingOccurrences(of: "\\", with: "\\\\")
             .replacingOccurrences(of: "\"", with: "\\\"")
 
+        // Resolve the iMessage service by iterating with a per-service `try`.
+        // A plain `1st service whose service type = iMessage` throws (-1728)
+        // when any stale service errors on `service type`, and it would also
+        // pick a *disabled* service. Require an enabled iMessage service; if
+        // none, fail with a clear reason instead of a cryptic delivery error.
         let script = """
         tell application "Messages"
-            set targetService to 1st service whose service type = iMessage
+            set targetService to missing value
+            repeat with s in services
+                try
+                    if (service type of s) is iMessage and (enabled of s) then
+                        set targetService to s
+                        exit repeat
+                    end if
+                end try
+            end repeat
+            if targetService is missing value then error "no enabled iMessage service"
             set targetBuddy to buddy "\(sanitizedBuddy)" of targetService
             send "\(sanitizedBody)" to targetBuddy
         end tell
@@ -143,6 +157,17 @@ class SendService {
             return (false, nil, errorMessage)
         }
 
+        // osascript exiting 0 only means Messages accepted the command — NOT
+        // that the message transmitted. Verify against chat.db: a disabled
+        // iMessage service still creates a message row, but with error != 0
+        // (e.g. error 33). Never report success the ground truth contradicts.
+        Thread.sleep(forTimeInterval: 4)
+        if let sendError = Self.chatDBSendError(buddyId: buddyId), sendError != 0 {
+            osLog.error("send: chat.db reports error=\(sendError, privacy: .public) for \(logPrefix, privacy: .public) — NOT delivered")
+            activityLog.error("iMessage send failed to \(logPrefix)...: Messages error \(sendError)")
+            return (false, nil, "Messages reported error \(sendError) — not delivered (iMessage service may be disabled)")
+        }
+
         dailySendCount += 1
         hourlySendCount += 1
 
@@ -192,6 +217,27 @@ class SendService {
         }
     }
 
+    /// Most-recent outbound `message.error` for `buddyId` from chat.db, or nil
+    /// if no row is found. A non-zero value means Messages failed the send
+    /// even when `osascript` exited 0 (e.g. disabled iMessage service → 33).
+    nonisolated static func chatDBSendError(buddyId: String) -> Int? {
+        guard let dbQueue = iMessageReader.shared.getDatabaseQueue() else { return nil }
+        let suffix = String(buddyId.suffix(7))
+        let value: Int? = (try? dbQueue.read { db -> Int? in
+            guard let row = try Row.fetchOne(db, sql: """
+                SELECT m.error AS err
+                FROM message m
+                JOIN handle h ON h.ROWID = m.handle_id
+                WHERE m.is_from_me = 1 AND h.id LIKE ?
+                ORDER BY m.date DESC
+                LIMIT 1
+                """, arguments: ["%\(suffix)"])
+            else { return nil }
+            return (row["err"] as? Int64).map(Int.init)
+        }) ?? nil
+        return value
+    }
+
     func getRateLimitStatus() -> (dailyRemaining: Int, hourlyRemaining: Int) {
         resetCountersIfNeeded()
         return (max(0, maxDailyMessages - dailySendCount), max(0, maxHourlyMessages - hourlySendCount))