diff --git a/lib/base/application.cpp b/lib/base/application.cpp
index 5856cba98a4..89a3c8f76e9 100644
--- a/lib/base/application.cpp
+++ b/lib/base/application.cpp
@@ -15,10 +15,12 @@
 #include "base/scriptglobal.hpp"
 #include "base/process.hpp"
 #include "base/tlsutility.hpp"
+#include <algorithm>
 #include <boost/algorithm/string/trim.hpp>
 #include <boost/exception/errinfo_api_function.hpp>
 #include <boost/exception/errinfo_errno.hpp>
 #include <boost/exception/errinfo_file_name.hpp>
+#include <cstring>
 #include <sstream>
 #include <iostream>
 #include <fstream>
@@ -56,11 +58,12 @@ double Application::m_StartTime;
 bool Application::m_ScriptDebuggerEnabled = false;
 
 #ifdef _WIN32
-double Application::m_LastReloadFailed = 0;
+Application::LastFailedReload Application::m_LastReloadFailed;
+std::mutex Application::m_LastReloadFailedMutex;
 #else /* _WIN32 */
-std::atomic<double>* Application::m_LastReloadFailed = ([]() -> std::atomic<double>* {
+Application::LastFailedReload* Application::m_LastReloadFailed = ([]() -> Application::LastFailedReload* {
 	auto memory (mmap(
-		nullptr, sizeof(std::atomic<double>),
+		nullptr, sizeof(Application::LastFailedReload),
 		PROT_READ | PROT_WRITE, MAP_ANONYMOUS | MAP_SHARED, -1, 0
 	));
 	if (memory == MAP_FAILED) {
@@ -69,8 +72,11 @@ std::atomic<double>* Application::m_LastReloadFailed = ([]() -> std::atomic<doub
 			<< boost::errinfo_errno(errno));
 	}
 
-	auto lrf ((std::atomic<double>*)memory);
-	lrf->store(0);
+	auto lrf ((Application::LastFailedReload*)memory);
+
+	lrf->When.store(0);
+	std::fill((volatile char*)lrf->Why, (volatile char*)lrf->Why + sizeof(lrf->Why), 0);
+
 	return lrf;
 })();
 #endif /* _WIN32 */
@@ -383,7 +389,7 @@ void Application::OnShutdown()
 static void ReloadProcessCallbackInternal(const ProcessResult& pr)
 {
 	if (pr.ExitStatus != 0) {
-		Application::SetLastReloadFailed(Utility::GetTime());
+		Application::SetLastReloadFailed(Utility::GetTime(), pr.Output);
 		Log(LogCritical, "Application", "Found error in config: reloading aborted");
 	}
 #ifdef _WIN32
@@ -1188,21 +1194,30 @@ void Application::SetScriptDebuggerEnabled(bool enabled)
 	m_ScriptDebuggerEnabled = enabled;
 }
 
-double Application::GetLastReloadFailed()
+std::pair<double, String> Application::GetLastReloadFailed()
 {
 #ifdef _WIN32
-	return m_LastReloadFailed;
+	std::unique_lock<std::mutex> lock (m_LastReloadFailedMutex);
+	return std::pair<double, String>(m_LastReloadFailed.When, m_LastReloadFailed.Why);
 #else /* _WIN32 */
-	return m_LastReloadFailed->load();
+	char reason[sizeof(m_LastReloadFailed->Why)];
+	std::copy((volatile char*)m_LastReloadFailed->Why, (volatile char*)m_LastReloadFailed->Why + sizeof(m_LastReloadFailed->Why), (char*)reason);
+
+	return std::pair<double, String>(m_LastReloadFailed->When.load(), String((char*)reason));
 #endif /* _WIN32 */
 }
 
-void Application::SetLastReloadFailed(double ts)
+void Application::SetLastReloadFailed(double ts, const String& reason)
 {
 #ifdef _WIN32
-	m_LastReloadFailed = ts;
+	std::unique_lock<std::mutex> lock (m_LastReloadFailedMutex);
+	m_LastReloadFailed = LastFailedReload{ts, reason};
 #else /* _WIN32 */
-	m_LastReloadFailed->store(ts);
+	char buf[sizeof(m_LastReloadFailed->Why)] = {0};
+
+	(void)strncpy((char*)buf, reason.CStr(), sizeof(buf));
+	std::copy((char*)buf, (char*)buf + sizeof(buf), (volatile char*)m_LastReloadFailed->Why);
+	m_LastReloadFailed->When.store(ts);
 #endif /* _WIN32 */
 }
 
diff --git a/lib/base/application.hpp b/lib/base/application.hpp
index 3fe9a8e2400..8ea75c1f626 100644
--- a/lib/base/application.hpp
+++ b/lib/base/application.hpp
@@ -9,6 +9,8 @@
 #include "base/configuration.hpp"
 #include <atomic>
 #include <iosfwd>
+#include <mutex>
+#include <utility>
 
 namespace icinga
 {
@@ -101,8 +103,8 @@ class Application : public ObjectImpl<Application> {
 	static bool GetScriptDebuggerEnabled();
 	static void SetScriptDebuggerEnabled(bool enabled);
 
-	static double GetLastReloadFailed();
-	static void SetLastReloadFailed(double ts);
+	static std::pair<double, String> GetLastReloadFailed();
+	static void SetLastReloadFailed(double ts, const String& reason);
 
 	static void DisplayInfoMessage(std::ostream& os, bool skipVersion = false);
 
@@ -138,10 +140,24 @@ class Application : public ObjectImpl<Application> {
 	static double m_StartTime;
 	static double m_MainTime;
 	static bool m_ScriptDebuggerEnabled;
+
 #ifdef _WIN32
-	static double m_LastReloadFailed;
+	struct LastFailedReload
+	{
+		double When = 0;
+		String Why;
+	};
+
+	static LastFailedReload m_LastReloadFailed;
+	static std::mutex m_LastReloadFailedMutex;
 #else /* _WIN32 */
-	static std::atomic<double> *m_LastReloadFailed;
+	struct LastFailedReload
+	{
+		std::atomic<double> When;
+		volatile char Why[4096];
+	};
+
+	static LastFailedReload *m_LastReloadFailed;
 #endif /* _WIN32 */
 
 #ifdef _WIN32
diff --git a/lib/cli/daemoncommand.cpp b/lib/cli/daemoncommand.cpp
index 92b87e5f8b9..7c0a052020f 100644
--- a/lib/cli/daemoncommand.cpp
+++ b/lib/cli/daemoncommand.cpp
@@ -10,6 +10,7 @@
 #include "base/atomic.hpp"
 #include "base/defer.hpp"
 #include "base/logger.hpp"
+#include "base/streamlogger.hpp"
 #include "base/application.hpp"
 #include "base/timer.hpp"
 #include "base/utility.hpp"
@@ -23,6 +24,7 @@
 #include <boost/program_options.hpp>
 #include <iostream>
 #include <fstream>
+#include <sstream>
 
 #ifdef _WIN32
 #include <windows.h>
@@ -233,6 +235,12 @@ int RunWorker(const std::vector<std::string>& configs, bool closeConsoleLog = fa
 	}
 #endif /* I2_DEBUG */
 
+	std::ostringstream oss;
+	StreamLogger::Ptr sl = new StreamLogger();
+
+	sl->BindStream(&oss, false);
+	sl->Start(true);
+
 	Log(LogInformation, "cli", "Loading configuration file(s).");
 
 	{
@@ -240,9 +248,18 @@ int RunWorker(const std::vector<std::string>& configs, bool closeConsoleLog = fa
 
 		if (!DaemonUtility::LoadConfigFiles(configs, newItems, Configuration::ObjectsPath, Configuration::VarsPath)) {
 			Log(LogCritical, "cli", "Config validation failed. Re-run with 'icinga2 daemon -C' after fixing the config.");
+
+			sl->Stop(true);
+			sl = nullptr;
+			Application::SetLastReloadFailed(Utility::GetTime(), oss.str());
+
 			return EXIT_FAILURE;
 		}
 
+		sl->Stop(true);
+		sl = nullptr;
+		oss = decltype(oss)();
+
 #ifndef _WIN32
 		Log(LogNotice, "cli")
 			<< "Notifying umbrella process (PID " << l_UmbrellaPid << ") about the config loading success";
@@ -477,6 +494,7 @@ static pid_t StartUnixWorker(const std::vector<std::string>& configs, bool close
 			}
 
 			(void)sigprocmask(SIG_UNBLOCK, &l_UnixWorkerSignals, nullptr);
+			Application::SetLastReloadFailed(Utility::GetTime(), "fork() failed");
 			return -1;
 
 		case 0:
@@ -511,11 +529,13 @@ static pid_t StartUnixWorker(const std::vector<std::string>& configs, bool close
 				} catch (const std::exception& ex) {
 					Log(LogCritical, "cli")
 						<< "Failed to re-initialize thread pool after forking (child): " << DiagnosticInformation(ex);
+					Application::SetLastReloadFailed(Utility::GetTime(), "Failed to re-initialize thread pool after forking (child)");
 					_exit(EXIT_FAILURE);
 				}
 
 				_exit(RunWorker(configs, closeConsoleLog, stderrFile));
 			} catch (...) {
+				Application::SetLastReloadFailed(Utility::GetTime(), "");
 				_exit(EXIT_FAILURE);
 			}
 
@@ -767,12 +787,11 @@ int DaemonCommand::Run(const po::variables_map& vm, const std::vector<std::strin
 
 			if (nextWorker == -1) {
 				Log(LogCritical, "Application", "Found error in config: reloading aborted");
-				Application::SetLastReloadFailed(Utility::GetTime());
 			} else {
 				Log(LogInformation, "Application")
 					<< "Reload done, old process shutting down. Child process with PID '" << nextWorker << "' is taking over.";
 
-				Application::SetLastReloadFailed(0);
+				Application::SetLastReloadFailed(0, "");
 				(void)kill(currentWorker, SIGTERM);
 
 				{