diff --git a/lib/base/io-engine.cpp b/lib/base/io-engine.cpp
index 2727236ad..246a448f2 100644
--- a/lib/base/io-engine.cpp
+++ b/lib/base/io-engine.cpp
@@ -148,6 +148,8 @@ void AsioConditionVariable::Wait(boost::asio::yield_context yc)
 
 void Timeout::Cancel()
 {
+	m_Cancelled->store(true);
+
 	boost::system::error_code ec;
 	m_Timer.cancel(ec);
 }
diff --git a/lib/base/io-engine.hpp b/lib/base/io-engine.hpp
index a030d2044..919f773bc 100644
--- a/lib/base/io-engine.hpp
+++ b/lib/base/io-engine.hpp
@@ -3,10 +3,12 @@
 #ifndef IO_ENGINE_H
 #define IO_ENGINE_H
 
+#include "base/atomic.hpp"
 #include "base/debug.hpp"
 #include "base/exception.hpp"
 #include "base/lazy-init.hpp"
 #include "base/logger.hpp"
+#include "base/shared.hpp"
 #include "base/shared-object.hpp"
 #include <atomic>
 #include <exception>
@@ -174,21 +176,29 @@ public:
 
 	template<class OnTimeout>
 	Timeout(boost::asio::io_context::strand& strand, const Timer::duration_type& timeoutFromNow, OnTimeout onTimeout)
-		: m_Timer(strand.context(), timeoutFromNow)
+		: m_Timer(strand.context(), timeoutFromNow), m_Cancelled(Shared<Atomic<bool>>::Make(false))
 	{
 		VERIFY(strand.running_in_this_thread());
 
-		m_Timer.async_wait(boost::asio::bind_executor(strand, [onTimeout = std::move(onTimeout)](boost::system::error_code ec) {
-			if (!ec) {
-				onTimeout();
+		m_Timer.async_wait(boost::asio::bind_executor(
+			strand, [cancelled = m_Cancelled, onTimeout = std::move(onTimeout)](boost::system::error_code ec) {
+				if (!ec && !cancelled->load()) {
+					onTimeout();
+				}
 			}
-		}));
+		));
+	}
+
+	~Timeout() override
+	{
+		Cancel();
 	}
 
 	void Cancel();
 
 private:
 	Timer m_Timer;
+	Shared<Atomic<bool>>::Ptr m_Cancelled;
 };
 
 }
diff --git a/test/base-io-engine.cpp b/test/base-io-engine.cpp
index 74cb67319..d75ce706d 100644
--- a/test/base-io-engine.cpp
+++ b/test/base-io-engine.cpp
@@ -5,6 +5,7 @@
 #include <boost/asio.hpp>
 #include <boost/date_time/posix_time/posix_time.hpp>
 #include <BoostTestTargetConfig.h>
+#include <thread>
 
 using namespace icinga;
 
@@ -30,7 +31,10 @@ BOOST_AUTO_TEST_CASE(timeout_run)
 		timer.async_wait(yc);
 	});
 
+	std::thread eventLoop ([&io] { io.run(); });
 	io.run();
+	eventLoop.join();
+
 	BOOST_CHECK_EQUAL(called, 1);
 }
 
@@ -54,7 +58,10 @@ BOOST_AUTO_TEST_CASE(timeout_cancelled)
 		timer.async_wait(yc);
 	});
 
+	std::thread eventLoop ([&io] { io.run(); });
 	io.run();
+	eventLoop.join();
+
 	BOOST_CHECK_EQUAL(called, 0);
 }
 
@@ -80,7 +87,10 @@ BOOST_AUTO_TEST_CASE(timeout_scope)
 		timer.async_wait(yc);
 	});
 
+	std::thread eventLoop ([&io] { io.run(); });
 	io.run();
+	eventLoop.join();
+
 	BOOST_CHECK_EQUAL(called, 0);
 }
 
@@ -108,7 +118,10 @@ BOOST_AUTO_TEST_CASE(timeout_due_cancelled)
 		timer.async_wait(yc);
 	});
 
+	std::thread eventLoop ([&io] { io.run(); });
 	io.run();
+	eventLoop.join();
+
 	BOOST_CHECK_EQUAL(called, 0);
 }
 
@@ -136,7 +149,10 @@ BOOST_AUTO_TEST_CASE(timeout_due_scope)
 		timer.async_wait(yc);
 	});
 
+	std::thread eventLoop ([&io] { io.run(); });
 	io.run();
+	eventLoop.join();
+
 	BOOST_CHECK_EQUAL(called, 0);
 }