diff --git a/src/crystal/system/win32/iocp.cr b/src/crystal/system/win32/iocp.cr
index ba0f11eb2af5..add5a29c2814 100644
--- a/src/crystal/system/win32/iocp.cr
+++ b/src/crystal/system/win32/iocp.cr
@@ -65,15 +65,11 @@ module Crystal::IOCP
     enum State
       STARTED
       DONE
-      CANCELLED
     end
 
     @overlapped = LibC::OVERLAPPED.new
     @fiber = Fiber.current
     @state : State = :started
-    property next : OverlappedOperation?
-    property previous : OverlappedOperation?
-    @@canceled = Thread::LinkedList(OverlappedOperation).new
 
     def initialize(@handle : LibC::HANDLE)
     end
@@ -83,12 +79,9 @@ module Crystal::IOCP
     end
 
     def self.run(handle, &)
-      operation = OverlappedOperation.new(handle)
-      begin
-        yield operation
-      ensure
-        operation.done
-      end
+      operation_storage = uninitialized ReferenceStorage(OverlappedOperation)
+      operation = OverlappedOperation.unsafe_construct(pointerof(operation_storage), handle)
+      yield operation
     end
 
     def self.unbox(overlapped : LibC::OVERLAPPED*)
@@ -103,8 +96,6 @@ module Crystal::IOCP
     def wait_for_result(timeout, &)
       wait_for_completion(timeout)
 
-      raise Exception.new("Invalid state #{@state}") unless @state.done? || @state.started?
-
       result = LibC.GetOverlappedResult(@handle, self, out bytes, 0)
       if result.zero?
         error = WinError.value
@@ -118,11 +109,7 @@ module Crystal::IOCP
 
     def wait_for_wsa_result(timeout, &)
       wait_for_completion(timeout)
-      wsa_result { |error| yield error }
-    end
 
-    def wsa_result(&)
-      raise Exception.new("Invalid state #{@state}") unless @state.done? || @state.started?
       flags = 0_u32
       result = LibC.WSAGetOverlappedResult(LibC::SOCKET.new(@handle.address), self, out bytes, false, pointerof(flags))
       if result.zero?
@@ -136,49 +123,48 @@ module Crystal::IOCP
     end
 
     protected def schedule(&)
-      case @state
-      when .started?
-        yield @fiber
-        done!
-      when .cancelled?
-        @@canceled.delete(self)
-      else
-        raise Exception.new("Invalid state #{@state}")
-      end
-    end
-
-    protected def done
-      case @state
-      when .started?
-        # https://learn.microsoft.com/en-us/windows/win32/api/ioapiset/nf-ioapiset-cancelioex
-        # > The application must not free or reuse the OVERLAPPED structure
-        # associated with the canceled I/O operations until they have completed
-        if LibC.CancelIoEx(@handle, self) != 0
-          @state = :cancelled
-          @@canceled.push(self) # to increase lifetime
-        end
-      end
+      done!
+      yield @fiber
     end
 
     def done!
+      @fiber.cancel_timeout
       @state = :done
     end
 
+    def try_cancel : Bool
+      # Microsoft documentation:
+      # The application must not free or reuse the OVERLAPPED structure
+      # associated with the canceled I/O operations until they have completed
+      # (this does not apply to asynchronous operations that finished
+      # synchronously, as nothing would be queued to the IOCP)
+      ret = LibC.CancelIoEx(@handle, self)
+      if ret.zero?
+        case error = WinError.value
+        when .error_not_found?
+          # Operation has already completed, do nothing
+          return false
+        else
+          raise RuntimeError.from_os_error("CancelIOEx", os_error: error)
+        end
+      end
+      true
+    end
+
     def wait_for_completion(timeout)
       if timeout
-        timeout_event = Crystal::IOCP::Event.new(Fiber.current)
-        timeout_event.add(timeout)
+        sleep timeout
       else
-        timeout_event = Crystal::IOCP::Event.new(Fiber.current, Time::Span::MAX)
+        Fiber.suspend
       end
-      # memoize event loop to make sure that we still target the same instance
-      # after wakeup (guaranteed by current MT model but let's be future proof)
-      event_loop = Crystal::EventLoop.current
-      event_loop.enqueue(timeout_event)
-
-      Fiber.suspend
 
-      event_loop.dequeue(timeout_event)
+      unless @state.done?
+        if try_cancel
+          # Wait for cancellation to complete. We must not free the operation
+          # until it's completed.
+          Fiber.suspend
+        end
+      end
     end
   end
 
@@ -200,13 +186,12 @@ module Crystal::IOCP
           raise IO::Error.from_os_error(method, error, target: target)
         end
       else
-        operation.done!
         return value
       end
 
       operation.wait_for_result(timeout) do |error|
         case error
-        when .error_io_incomplete?
+        when .error_io_incomplete?, .error_operation_aborted?
           raise IO::TimeoutError.new("#{method} timed out")
         when .error_handle_eof?
           return 0_u32
@@ -230,13 +215,12 @@ module Crystal::IOCP
           raise IO::Error.from_os_error(method, error, target: target)
         end
       else
-        operation.done!
         return value
       end
 
       operation.wait_for_wsa_result(timeout) do |error|
         case error
-        when .wsa_io_incomplete?
+        when .wsa_io_incomplete?, .error_operation_aborted?
           raise IO::TimeoutError.new("#{method} timed out")
         when .wsaeconnreset?
           return 0_u32 unless connreset_is_error
diff --git a/src/crystal/system/win32/socket.cr b/src/crystal/system/win32/socket.cr
index 2a540f4df88d..9bf1fd6ac853 100644
--- a/src/crystal/system/win32/socket.cr
+++ b/src/crystal/system/win32/socket.cr
@@ -142,7 +142,6 @@ module Crystal::System::Socket
           return ::Socket::Error.from_os_error("ConnectEx", error)
         end
       else
-        operation.done!
         return nil
       end
 
@@ -204,18 +203,15 @@ module Crystal::System::Socket
           return false
         end
       else
-        operation.done!
         return true
       end
 
-      unless operation.wait_for_completion(read_timeout)
-        raise IO::TimeoutError.new("#{method} timed out")
-      end
-
-      operation.wsa_result do |error|
+      operation.wait_for_wsa_result(read_timeout) do |error|
         case error
         when .wsa_io_incomplete?, .wsaenotsock?
           return false
+        when .error_operation_aborted?
+          raise IO::TimeoutError.new("#{method} timed out")
         end
       end