diff --git a/StikDebug/Device/JITEnableContext.swift b/StikDebug/Device/JITEnableContext.swift
index a63c5e7..9448486 100644
--- a/StikDebug/Device/JITEnableContext.swift
+++ b/StikDebug/Device/JITEnableContext.swift
@@ -126,7 +126,8 @@ final class JITEnableContext {
         }
 
         if let ffiError {
-            throw error(from: ffiError, fallback: "Failed to read pairing file!")
+            let readError = error(from: ffiError, fallback: "Failed to read pairing file!")
+            throw Self.isMalformedPairingFile(readError) ? malformedPairingFileError(readError) : readError
         }
 
         guard let pairingFile else {
@@ -136,6 +137,24 @@ final class JITEnableContext {
         return pairingFile
     }
 
+    /// `rp_pairing_file_read` only parses the local plist on disk — no network
+    /// involved — so a Serde/plist error here always means the file's contents
+    /// are the wrong shape (e.g. an older pairing file missing `public_key`),
+    /// not a transient failure a retry would fix. Reclassifying it to the same
+    /// code as an invalid pairing file routes it to the "select a new file"
+    /// prompt instead of the generic connection-error/retry flow.
+    private static func isMalformedPairingFile(_ error: NSError) -> Bool {
+        let message = error.localizedDescription.lowercased()
+        return message.contains("missing field") || message.contains("serde(") || message.contains("plist(error")
+    }
+
+    private func malformedPairingFileError(_ underlying: NSError) -> NSError {
+        makeError(
+            "The pairing file is missing data StikDebug needs (\(underlying.localizedDescription)). It's likely the wrong format or an incomplete export — select a new pairing file.",
+            code: -9
+        )
+    }
+
     private func createTunnel(hostname: String) throws -> TunnelHandles {
         let pairingFile = try getPairingFile()
         defer { rp_pairing_file_free(pairingFile) }