diff --git a/Sources/Containerization/VZVirtualMachine+Helpers.swift b/Sources/Containerization/VZVirtualMachine+Helpers.swift
index 135ca019..a3bbfed7 100644
--- a/Sources/Containerization/VZVirtualMachine+Helpers.swift
+++ b/Sources/Containerization/VZVirtualMachine+Helpers.swift
@@ -139,8 +139,11 @@ extension VZVirtualMachine {
 }
 
 extension VZVirtioSocketConnection {
-    func dupHandle() -> FileHandle {
+    func dupHandle() throws -> FileHandle {
         let fd = dup(self.fileDescriptor)
+        if fd == -1 {
+            throw POSIXError.fromErrno()
+        }
         self.close()
         return FileHandle(fileDescriptor: fd, closeOnDealloc: false)
     }
diff --git a/Sources/Containerization/VZVirtualMachineInstance.swift b/Sources/Containerization/VZVirtualMachineInstance.swift
index 035009e8..a4364c4f 100644
--- a/Sources/Containerization/VZVirtualMachineInstance.swift
+++ b/Sources/Containerization/VZVirtualMachineInstance.swift
@@ -195,25 +195,47 @@ extension VZVirtualMachineInstance: VirtualMachineInstance {
 
     public func dialAgent() async throws -> Vminitd {
         try await lock.withLock { connections in
-            let handle = try await vm.connect(
-                queue: queue,
-                port: Vminitd.port
-            ).dupHandle()
+            do {
+                let conn = try await vm.connect(
+                    queue: queue,
+                    port: Vminitd.port
+                )
+                let handle = try conn.dupHandle()
+                let agent = Vminitd(connection: handle, group: self.group)
+                connections.agents.append(agent)
 
-            let agent = Vminitd(connection: handle, group: self.group)
-            connections.agents.append(agent)
-
-            return agent
+                return agent
+            } catch {
+                if let err = error as? ContainerizationError {
+                    throw err
+                }
+                throw ContainerizationError(
+                    .internalError,
+                    message: "failed to dial agent",
+                    cause: error
+                )
+            }
         }
     }
 
     func dial(_ port: UInt32) async throws -> FileHandle {
         try await lock.withLock { connections in
-            let handle = try await vm.connect(
-                queue: queue,
-                port: port
-            ).dupHandle()
-            return handle
+            do {
+                let conn = try await vm.connect(
+                    queue: queue,
+                    port: port
+                )
+                return try conn.dupHandle()
+            } catch {
+                if let err = error as? ContainerizationError {
+                    throw err
+                }
+                throw ContainerizationError(
+                    .internalError,
+                    message: "failed to dial vsock port",
+                    cause: error
+                )
+            }
         }
     }