diff --git a/CMakeLists.txt b/CMakeLists.txt
index 7331f0cf6..a974a817d 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -196,10 +196,6 @@ include_directories(
   ${CMAKE_CURRENT_BINARY_DIR} ${CMAKE_CURRENT_BINARY_DIR}/lib
 )
 
-if(HAVE_LIBEXECINFO)
-  list(APPEND base_DEPS execinfo)
-endif()
-
 if(UNIX OR CYGWIN)
   list(APPEND base_OBJS $<TARGET_OBJECTS:execvpe>)
 endif()
@@ -359,6 +355,20 @@ check_include_file_cxx(cxxabi.h HAVE_CXXABI_H)
 
 if(HAVE_LIBEXECINFO)
   set(HAVE_BACKTRACE_SYMBOLS TRUE)
+  list(APPEND base_DEPS execinfo)
+endif()
+
+if(NOT WIN32)
+  # boost::stacktrace uses _Unwind_Backtrace which is only exposed if _GNU_SOURCE is defined on most systems
+  add_definitions(-D_GNU_SOURCE)
+endif()
+
+if(CMAKE_SYSTEM_NAME STREQUAL "FreeBSD")
+  set(ICINGA2_STACKTRACE_USE_BACKTRACE_SYMBOLS TRUE)
+endif()
+
+if(ICINGA2_STACKTRACE_USE_BACKTRACE_SYMBOLS AND NOT HAVE_BACKTRACE_SYMBOLS)
+  message(FATAL_ERROR "ICINGA2_STACKTRACE_USE_BACKTRACE_SYMBOLS is set but backtrace_symbols() was not found")
 endif()
 
 if(CMAKE_CXX_COMPILER_ID STREQUAL "GNU")
@@ -372,6 +382,12 @@ if(CMAKE_CXX_COMPILER_ID STREQUAL "GNU")
   endif()
 endif()
 
+if(MSVC)
+  if("${CMAKE_CXX_COMPILER_VERSION}" VERSION_LESS "19.20")
+    message(FATAL_ERROR "Your version of MSVC (${CMAKE_CXX_COMPILER_VERSION}) is too old for building Icinga 2 (MSVC >= 19.20 from Visual Studio 2019 is required).")
+  endif()
+endif()
+
 if(NOT MSVC)
   set(CMAKE_CXX_FLAGS "${CMAKE_CXX_FLAGS} -std=c++0x")
 
diff --git a/config.h.cmake b/config.h.cmake
index 16fa190f1..3ed2ae46d 100644
--- a/config.h.cmake
+++ b/config.h.cmake
@@ -12,6 +12,7 @@
 #cmakedefine HAVE_SYSTEMD
 
 #cmakedefine ICINGA2_UNITY_BUILD
+#cmakedefine ICINGA2_STACKTRACE_USE_BACKTRACE_SYMBOLS
 
 #define ICINGA_CONFIGDIR "${ICINGA2_FULL_CONFIGDIR}"
 #define ICINGA_DATADIR "${ICINGA2_FULL_DATADIR}"
diff --git a/doc/21-development.md b/doc/21-development.md
index 7872a3b48..724d156d4 100644
--- a/doc/21-development.md
+++ b/doc/21-development.md
@@ -1119,6 +1119,7 @@ General:
 - [function_types](https://www.boost.org/doc/libs/1_66_0/libs/function_types/doc/html/index.html) (header only)
 - [circular_buffer](https://www.boost.org/doc/libs/1_66_0/doc/html/circular_buffer.html) (header only)
 - [math](https://www.boost.org/doc/libs/1_66_0/libs/math/doc/html/index.html) (header only)
+- [stacktrace](https://www.boost.org/doc/libs/1_66_0/doc/html/stacktrace.html) (header only)
 
 Events and Runtime:
 
diff --git a/lib/base/application.cpp b/lib/base/application.cpp
index e8fd04704..c6b31910d 100644
--- a/lib/base/application.cpp
+++ b/lib/base/application.cpp
@@ -18,6 +18,7 @@
 #include <boost/exception/errinfo_api_function.hpp>
 #include <boost/exception/errinfo_errno.hpp>
 #include <boost/exception/errinfo_file_name.hpp>
+#include <boost/stacktrace.hpp>
 #include <sstream>
 #include <iostream>
 #include <fstream>
@@ -33,6 +34,14 @@
 
 using namespace icinga;
 
+#ifdef _WIN32
+/* MSVC throws unhandled C++ exceptions as SEH exceptions with this specific error code.
+ * There seems to be no system header that actually defines this constant.
+ * See also https://devblogs.microsoft.com/oldnewthing/20160915-00/?p=94316
+ */
+#define EXCEPTION_CODE_CXX_EXCEPTION 0xe06d7363
+#endif /* _WIN32 */
+
 REGISTER_TYPE(Application);
 
 boost::signals2::signal<void ()> Application::OnReopenLogs;
@@ -54,6 +63,10 @@ double Application::m_StartTime;
 bool Application::m_ScriptDebuggerEnabled = false;
 double Application::m_LastReloadFailed;
 
+#ifdef _WIN32
+static LPTOP_LEVEL_EXCEPTION_FILTER l_DefaultUnhandledExceptionFilter = nullptr;
+#endif /* _WIN32 */
+
 /**
  * Constructor for the Application class.
  */
@@ -742,11 +755,12 @@ void Application::SigAbrtHandler(int)
 		Log(LogCritical, "Application")
 			<< "Icinga 2 has terminated unexpectedly. Additional information can be found in '" << fname << "'" << "\n";
 
+		ofs << "Caught SIGABRT.\n"
+			<< "Current time: " << Utility::FormatDateTime("%Y-%m-%d %H:%M:%S %z", Utility::GetTime()) << "\n\n";
+
 		DisplayInfoMessage(ofs);
 
-		StackTrace trace;
-		ofs << "Stacktrace:" << "\n";
-		trace.Print(ofs, 1);
+		ofs << "\nStacktrace:\n" << StackTraceFormatter(boost::stacktrace::stacktrace()) << "\n";
 
 		DisplayBugMessage(ofs);
 
@@ -849,9 +863,8 @@ void Application::ExceptionHandler()
 		std::ofstream ofs;
 		ofs.open(fname.CStr());
 
-		ofs << "Caught unhandled exception." << "\n"
-			<< "Current time: " << Utility::FormatDateTime("%Y-%m-%d %H:%M:%S %z", Utility::GetTime()) << "\n"
-			<< "\n";
+		ofs << "Caught unhandled exception.\n"
+			<< "Current time: " << Utility::FormatDateTime("%Y-%m-%d %H:%M:%S %z", Utility::GetTime()) << "\n\n";
 
 		DisplayInfoMessage(ofs);
 
@@ -863,8 +876,19 @@ void Application::ExceptionHandler()
 				<< "\n"
 				<< "Additional information is available in '" << fname << "'" << "\n";
 
+			/* On platforms where HAVE_CXXABI_H is defined, we prefer to print the stack trace that was saved
+			 * when the last exception was thrown. Everywhere else, we do not have this information so we
+			 * collect a stack trace here, which might lack some information, for example when an exception
+			 * is rethrown, but this is still better than nothing.
+			 */
+			boost::stacktrace::stacktrace *stack = nullptr;
+#ifndef HAVE_CXXABI_H
+			boost::stacktrace::stacktrace local_stack;
+			stack = &local_stack;
+#endif /* HAVE_CXXABI_H */
+
 			ofs << "\n"
-				<< DiagnosticInformation(ex)
+				<< DiagnosticInformation(ex, true, stack)
 				<< "\n";
 		}
 
@@ -881,6 +905,15 @@ void Application::ExceptionHandler()
 #ifdef _WIN32
 LONG CALLBACK Application::SEHUnhandledExceptionFilter(PEXCEPTION_POINTERS exi)
 {
+	/* If an unhandled C++ exception occurs with both a termination handler (std::set_terminate()) and an unhandled
+	 * SEH filter (SetUnhandledExceptionFilter()) set, the latter one is called. However, our termination handler is
+	 * better suited for dealing with C++ exceptions. In this case, the SEH exception will have a specific code and
+	 * we can just call the default filter function which will take care of calling the termination handler.
+	 */
+	if (exi->ExceptionRecord->ExceptionCode == EXCEPTION_CODE_CXX_EXCEPTION) {
+		return l_DefaultUnhandledExceptionFilter(exi);
+	}
+
 	if (l_InExceptionHandler)
 		return EXCEPTION_CONTINUE_SEARCH;
 
@@ -905,15 +938,20 @@ LONG CALLBACK Application::SEHUnhandledExceptionFilter(PEXCEPTION_POINTERS exi)
 	Log(LogCritical, "Application")
 		<< "Icinga 2 has terminated unexpectedly. Additional information can be found in '" << fname << "'";
 
+	ofs << "Caught unhandled SEH exception.\n"
+		<< "Current time: " << Utility::FormatDateTime("%Y-%m-%d %H:%M:%S %z", Utility::GetTime()) << "\n\n";
+
 	DisplayInfoMessage(ofs);
 
-	ofs << "Caught unhandled SEH exception." << "\n"
-		<< "Current time: " << Utility::FormatDateTime("%Y-%m-%d %H:%M:%S %z", Utility::GetTime()) << "\n"
-		<< "\n";
+	std::ios::fmtflags savedflags(ofs.flags());
+	ofs << std::showbase << std::hex
+		<< "\nSEH exception:\n"
+		<< "  Code: "    << exi->ExceptionRecord->ExceptionCode    << "\n"
+		<< "  Address: " << exi->ExceptionRecord->ExceptionAddress << "\n"
+		<< "  Flags: "   << exi->ExceptionRecord->ExceptionFlags   << "\n";
+	ofs.flags(savedflags);
 
-	StackTrace trace(exi);
-	ofs << "Stacktrace:" << "\n";
-	trace.Print(ofs, 1);
+	ofs << "\nStacktrace:\n" << StackTraceFormatter(boost::stacktrace::stacktrace()) << "\n";
 
 	DisplayBugMessage(ofs);
 
@@ -934,7 +972,7 @@ void Application::InstallExceptionHandlers()
 	sa.sa_handler = &Application::SigAbrtHandler;
 	sigaction(SIGABRT, &sa, nullptr);
 #else /* _WIN32 */
-	SetUnhandledExceptionFilter(&Application::SEHUnhandledExceptionFilter);
+	l_DefaultUnhandledExceptionFilter = SetUnhandledExceptionFilter(&Application::SEHUnhandledExceptionFilter);
 #endif /* _WIN32 */
 }
 
diff --git a/lib/base/exception.cpp b/lib/base/exception.cpp
index c694b6bf2..2d5331f01 100644
--- a/lib/base/exception.cpp
+++ b/lib/base/exception.cpp
@@ -1,6 +1,7 @@
 /* Icinga 2 | (c) 2012 Icinga GmbH | GPLv2+ */
 
 #include "base/exception.hpp"
+#include "base/stacktrace.hpp"
 #include <boost/thread/tss.hpp>
 
 #ifdef _WIN32
@@ -13,7 +14,7 @@
 
 using namespace icinga;
 
-static boost::thread_specific_ptr<StackTrace> l_LastExceptionStack;
+static boost::thread_specific_ptr<boost::stacktrace::stacktrace> l_LastExceptionStack;
 static boost::thread_specific_ptr<ContextTrace> l_LastExceptionContext;
 
 #ifdef HAVE_CXXABI_H
@@ -32,6 +33,14 @@ public:
 
 
 #if defined(__GLIBCXX__) || defined(_LIBCPPABI_VERSION)
+/**
+ * Attempts to cast an exception to a destination type
+ *
+ * @param obj Exception to be casted
+ * @param src Type information of obj
+ * @param dst Information of which type to cast to
+ * @return Pointer to the exception if the cast is possible, nullptr otherwise
+ */
 inline void *cast_exception(void *obj, const std::type_info *src, const std::type_info *dst)
 {
 #ifdef __GLIBCXX__
@@ -92,6 +101,13 @@ void icinga::RethrowUncaughtException()
 extern "C"
 void __cxa_throw(void *obj, TYPEINFO_TYPE *pvtinfo, void (*dest)(void *))
 {
+	/* This function overrides an internal function of libstdc++ that is called when a C++ exception is thrown in order
+	 * to capture as much information as possible at that time and then call the original implementation. This
+	 * information includes:
+	 *  - stack trace (for later use in DiagnosticInformation)
+	 *  - context trace (for later use in DiagnosticInformation)
+	 */
+
 	auto *tinfo = static_cast<std::type_info *>(pvtinfo);
 
 	typedef void (*cxa_throw_fn)(void *, std::type_info *, void (*)(void *)) __attribute__((noreturn));
@@ -103,6 +119,7 @@ void __cxa_throw(void *obj, TYPEINFO_TYPE *pvtinfo, void (*dest)(void *))
 	l_LastExceptionDest.reset(new DestCallback(dest));
 #endif /* !defined(__GLIBCXX__) && !defined(_WIN32) */
 
+	// resolve symbol to original implementation of __cxa_throw for the call at the end of this function
 	if (real_cxa_throw == nullptr)
 		real_cxa_throw = (cxa_throw_fn)dlsym(RTLD_NEXT, "__cxa_throw");
 
@@ -112,10 +129,12 @@ void __cxa_throw(void *obj, TYPEINFO_TYPE *pvtinfo, void (*dest)(void *))
 
 	if (!uex) {
 #endif /* NO_CAST_EXCEPTION */
-		StackTrace stack;
+		// save the current stack trace in a thread-local variable
+		boost::stacktrace::stacktrace stack;
 		SetLastExceptionStack(stack);
 
 #ifndef NO_CAST_EXCEPTION
+		// save the current stack trace in the boost exception error info if the exception is a boost::exception
 		if (ex && !boost::get_error_info<StackTraceErrorInfo>(*ex))
 			*ex << StackTraceErrorInfo(stack);
 	}
@@ -125,6 +144,7 @@ void __cxa_throw(void *obj, TYPEINFO_TYPE *pvtinfo, void (*dest)(void *))
 	SetLastExceptionContext(context);
 
 #ifndef NO_CAST_EXCEPTION
+	// save the current context trace in the boost exception error info if the exception is a boost::exception
 	if (ex && !boost::get_error_info<ContextTraceErrorInfo>(*ex))
 		*ex << ContextTraceErrorInfo(context);
 #endif /* NO_CAST_EXCEPTION */
@@ -133,14 +153,14 @@ void __cxa_throw(void *obj, TYPEINFO_TYPE *pvtinfo, void (*dest)(void *))
 }
 #endif /* HAVE_CXXABI_H */
 
-StackTrace *icinga::GetLastExceptionStack()
+boost::stacktrace::stacktrace *icinga::GetLastExceptionStack()
 {
 	return l_LastExceptionStack.get();
 }
 
-void icinga::SetLastExceptionStack(const StackTrace& trace)
+void icinga::SetLastExceptionStack(const boost::stacktrace::stacktrace& trace)
 {
-	l_LastExceptionStack.reset(new StackTrace(trace));
+	l_LastExceptionStack.reset(new boost::stacktrace::stacktrace(trace));
 }
 
 ContextTrace *icinga::GetLastExceptionContext()
@@ -153,7 +173,7 @@ void icinga::SetLastExceptionContext(const ContextTrace& context)
 	l_LastExceptionContext.reset(new ContextTrace(context));
 }
 
-String icinga::DiagnosticInformation(const std::exception& ex, bool verbose, StackTrace *stack, ContextTrace *context)
+String icinga::DiagnosticInformation(const std::exception& ex, bool verbose, boost::stacktrace::stacktrace *stack, ContextTrace *context)
 {
 	std::ostringstream result;
 
@@ -215,34 +235,37 @@ String icinga::DiagnosticInformation(const std::exception& ex, bool verbose, Sta
 	const auto *pex = dynamic_cast<const posix_error *>(&ex);
 
 	if (!uex && !pex && verbose) {
-		const StackTrace *st = boost::get_error_info<StackTraceErrorInfo>(ex);
-
-		if (st) {
-			result << *st;
-		} else {
-			result << std::endl;
-
-			if (!stack)
-				stack = GetLastExceptionStack();
-
-			if (stack)
-				result << *stack;
+		// Print the first of the following stack traces (if any exists)
+		//   1. stack trace from boost exception error information
+		const boost::stacktrace::stacktrace *st = boost::get_error_info<StackTraceErrorInfo>(ex);
+		//   2. stack trace explicitly passed as a parameter
+		if (!st) {
+			st = stack;
+		}
+		//   3. stack trace saved when the last exception was thrown
+		if (!st) {
+			st = GetLastExceptionStack();
+		}
 
+		if (st && !st->empty()) {
+			result << "\nStacktrace:\n" << StackTraceFormatter(*st);
 		}
 	}
 
+	// Print the first of the following context traces (if any exists)
+	//   1. context trace from boost exception error information
 	const ContextTrace *ct = boost::get_error_info<ContextTraceErrorInfo>(ex);
+	//   2. context trace explicitly passed as a parameter
+	if (!ct) {
+		ct = context;
+	}
+	//   3. context trace saved when the last exception was thrown
+	if (!ct) {
+		ct = GetLastExceptionContext();
+	}
 
-	if (ct) {
-		result << *ct;
-	} else {
-		result << std::endl;
-
-		if (!context)
-			context = GetLastExceptionContext();
-
-		if (context)
-			result << *context;
+	if (ct && ct->GetLength() > 0) {
+		result << "\nContext:\n" << *ct;
 	}
 
 	return result.str();
@@ -250,8 +273,8 @@ String icinga::DiagnosticInformation(const std::exception& ex, bool verbose, Sta
 
 String icinga::DiagnosticInformation(const boost::exception_ptr& eptr, bool verbose)
 {
-	StackTrace *pt = GetLastExceptionStack();
-	StackTrace stack;
+	boost::stacktrace::stacktrace *pt = GetLastExceptionStack();
+	boost::stacktrace::stacktrace stack;
 
 	ContextTrace *pc = GetLastExceptionContext();
 	ContextTrace context;
diff --git a/lib/base/exception.hpp b/lib/base/exception.hpp
index 246c28a78..279b1d036 100644
--- a/lib/base/exception.hpp
+++ b/lib/base/exception.hpp
@@ -5,7 +5,6 @@
 
 #include "base/i2-base.hpp"
 #include "base/string.hpp"
-#include "base/stacktrace.hpp"
 #include "base/context.hpp"
 #include "base/debuginfo.hpp"
 #include "base/dictionary.hpp"
@@ -15,6 +14,7 @@
 #include <boost/exception/errinfo_file_name.hpp>
 #include <boost/exception/diagnostic_information.hpp>
 #include <boost/exception_ptr.hpp>
+#include <boost/stacktrace.hpp>
 
 #ifdef _WIN32
 #	include <boost/algorithm/string/trim.hpp>
@@ -76,15 +76,16 @@ private:
 	Dictionary::Ptr m_DebugHint;
 };
 
-StackTrace *GetLastExceptionStack();
-void SetLastExceptionStack(const StackTrace& trace);
+boost::stacktrace::stacktrace *GetLastExceptionStack();
+void SetLastExceptionStack(const boost::stacktrace::stacktrace& trace);
 
 ContextTrace *GetLastExceptionContext();
 void SetLastExceptionContext(const ContextTrace& context);
 
 void RethrowUncaughtException();
 
-typedef boost::error_info<StackTrace, StackTrace> StackTraceErrorInfo;
+struct errinfo_stacktrace_;
+typedef boost::error_info<struct errinfo_stacktrace_, boost::stacktrace::stacktrace> StackTraceErrorInfo;
 
 std::string to_string(const StackTraceErrorInfo&);
 
@@ -92,7 +93,27 @@ typedef boost::error_info<ContextTrace, ContextTrace> ContextTraceErrorInfo;
 
 std::string to_string(const ContextTraceErrorInfo& e);
 
-String DiagnosticInformation(const std::exception& ex, bool verbose = true, StackTrace *stack = nullptr, ContextTrace *context = nullptr);
+/**
+ * Generate diagnostic information about an exception
+ *
+ * The following information is gathered in the result:
+ *  - Exception error message
+ *  - Debug information about the Icinga config if the exception is a ValidationError
+ *  - Stack trace
+ *  - Context trace
+ *
+ *  Each, stack trace and the context trace, are printed if the they were saved in the boost exception error
+ *  information, are explicitly passed as a parameter, or were stored when the last exception was thrown. If multiple
+ *  of these exist, the first one is used.
+ *
+ * @param ex exception to print diagnostic information about
+ * @param verbose if verbose is set, a stack trace is added
+ * @param stack optionally supply a stack trace
+ * @param context optionally supply a context trace
+ * @return string containing the aforementioned information
+ */
+String DiagnosticInformation(const std::exception& ex, bool verbose = true,
+	boost::stacktrace::stacktrace *stack = nullptr, ContextTrace *context = nullptr);
 String DiagnosticInformation(const boost::exception_ptr& eptr, bool verbose = true);
 
 class posix_error : virtual public std::exception, virtual public boost::exception {
diff --git a/lib/base/stacktrace.cpp b/lib/base/stacktrace.cpp
index 81fdd3380..e3f15ceb7 100644
--- a/lib/base/stacktrace.cpp
+++ b/lib/base/stacktrace.cpp
@@ -1,8 +1,10 @@
-/* Icinga 2 | (c) 2012 Icinga GmbH | GPLv2+ */
+/* Icinga 2 | (c) 2020 Icinga GmbH | GPLv2+ */
 
+#include <base/i2-base.hpp>
 #include "base/stacktrace.hpp"
-#include "base/utility.hpp"
-#include "base/initialize.hpp"
+#include <iostream>
+#include <iomanip>
+#include <vector>
 
 #ifdef HAVE_BACKTRACE_SYMBOLS
 #	include <execinfo.h>
@@ -10,130 +12,32 @@
 
 using namespace icinga;
 
-#ifdef _MSC_VER
-#	pragma optimize("", off)
-#endif /* _MSC_VER */
-
-StackTrace::StackTrace()
+std::ostream &icinga::operator<<(std::ostream &os, const StackTraceFormatter &f)
 {
-#ifdef HAVE_BACKTRACE_SYMBOLS
-	m_Count = backtrace(m_Frames, sizeof(m_Frames) / sizeof(m_Frames[0]));
-#else /* HAVE_BACKTRACE_SYMBOLS */
-#	ifdef _WIN32
-	m_Count = CaptureStackBackTrace(0, sizeof(m_Frames) / sizeof(m_Frames), m_Frames, nullptr);
-#	else /* _WIN32 */
-	m_Count = 0;
-#	endif /* _WIN32 */
-#endif /* HAVE_BACKTRACE_SYMBOLS */
-}
+	/* In most cases, this operator<< just relies on the operator<< for the `boost::stacktrace::stacktrace` wrapped in
+	 * the `StackTraceFormatter`. But as this operator turned out to not work properly on some platforms, there is a
+	 * fallback implementation that can be enabled using the `-DICINGA2_STACKTRACE_USE_BACKTRACE_SYMBOLS` flag at
+	 * compile time. This will then switch to `backtrace_symbols()` from `<execinfo.h>` instead of the implementation
+	 * provided by Boost.
+	 */
 
-#ifdef _MSC_VER
-#	pragma optimize("", on)
-#endif /* _MSC_VER */
+	const boost::stacktrace::stacktrace &stack = f.m_Stack;
 
-#ifdef _WIN32
-StackTrace::StackTrace(PEXCEPTION_POINTERS exi)
-{
-	STACKFRAME64 frame;
-	int architecture;
+#ifdef ICINGA2_STACKTRACE_USE_BACKTRACE_SYMBOLS
+	std::vector<void *> addrs;
+	addrs.reserve(stack.size());
+	std::transform(stack.begin(), stack.end(), std::back_inserter(addrs), [](const boost::stacktrace::frame &f) {
+		return const_cast<void *>(f.address());
+	});
 
-#ifdef _WIN64
-	architecture = IMAGE_FILE_MACHINE_AMD64;
-
-	frame.AddrPC.Offset = exi->ContextRecord->Rip;
-	frame.AddrFrame.Offset = exi->ContextRecord->Rbp;
-	frame.AddrStack.Offset = exi->ContextRecord->Rsp;
-#else /* _WIN64 */
-	architecture = IMAGE_FILE_MACHINE_I386;
-
-	frame.AddrPC.Offset = exi->ContextRecord->Eip;
-	frame.AddrFrame.Offset = exi->ContextRecord->Ebp;
-	frame.AddrStack.Offset = exi->ContextRecord->Esp;
-#endif  /* _WIN64 */
-
-	frame.AddrPC.Mode = AddrModeFlat;
-	frame.AddrFrame.Mode = AddrModeFlat;
-	frame.AddrStack.Mode = AddrModeFlat;
-
-	m_Count = 0;
-
-	while (StackWalk64(architecture, GetCurrentProcess(), GetCurrentThread(),
-		&frame, exi->ContextRecord, nullptr, &SymFunctionTableAccess64,
-		&SymGetModuleBase64, nullptr) && m_Count < sizeof(m_Frames) / sizeof(m_Frames[0])) {
-		m_Frames[m_Count] = reinterpret_cast<void *>(frame.AddrPC.Offset);
-		m_Count++;
+	char **symbols = backtrace_symbols(addrs.data(), addrs.size());
+	for (size_t i = 0; i < addrs.size(); i++) {
+		os << std::setw(2) << i << "# " << symbols[i] << std::endl;
 	}
-}
-#endif /* _WIN32 */
-
-#ifdef _WIN32
-INITIALIZE_ONCE([]() {
-	(void) SymSetOptions(SYMOPT_UNDNAME | SYMOPT_LOAD_LINES);
-	(void) SymInitialize(GetCurrentProcess(), nullptr, TRUE);
-});
-#endif /* _WIN32 */
-
-/**
- * Prints a stacktrace to the specified stream.
- *
- * @param fp The stream.
- * @param ignoreFrames The number of stackframes to ignore (in addition to
- *        the one this function is executing in).
- * @returns true if the stacktrace was printed, false otherwise.
- */
-void StackTrace::Print(std::ostream& fp, int ignoreFrames) const
-{
-	fp << std::endl;
-
-#ifndef _WIN32
-#	ifdef HAVE_BACKTRACE_SYMBOLS
-	char **messages = backtrace_symbols(m_Frames, m_Count);
-
-	for (int i = ignoreFrames + 1; i < m_Count && messages; ++i) {
-		String message = messages[i];
-
-		char *sym_begin = strchr(messages[i], '(');
-
-		if (sym_begin) {
-			char *sym_end = strchr(sym_begin, '+');
-
-			if (sym_end) {
-				String sym = String(sym_begin + 1, sym_end);
-				String sym_demangled = Utility::DemangleSymbolName(sym);
-
-				if (sym_demangled.IsEmpty())
-					sym_demangled = "<unknown function>";
-
-				String path = String(messages[i], sym_begin);
-
-				size_t slashp = path.RFind("/");
-
-				if (slashp != String::NPos)
-					path = path.SubStr(slashp + 1);
-
-				message = path + ": " + sym_demangled + " (" + String(sym_end);
-			}
-		}
-
-		fp << "\t(" << i - ignoreFrames - 1 << ") " << message << std::endl;
-	}
-
-	std::free(messages);
-
-	fp << std::endl;
-#	else /* HAVE_BACKTRACE_SYMBOLS */
-	fp << "(not available)" << std::endl;
-#	endif /* HAVE_BACKTRACE_SYMBOLS */
-#else /* _WIN32 */
-	for (int i = ignoreFrames + 1; i < m_Count; i++) {
-		fp << "\t(" << i - ignoreFrames - 1 << "): " << Utility::GetSymbolName(m_Frames[i]) << std::endl;
-	}
-#endif /* _WIN32 */
-}
-
-std::ostream& icinga::operator<<(std::ostream& stream, const StackTrace& trace)
-{
-	trace.Print(stream, 1);
-
-	return stream;
+	std::free(symbols);
+#else /* ICINGA2_STACKTRACE_USE_BACKTRACE_SYMBOLS */
+	os << stack;
+#endif /* ICINGA2_STACKTRACE_USE_BACKTRACE_SYMBOLS */
+
+	return os;
 }
diff --git a/lib/base/stacktrace.hpp b/lib/base/stacktrace.hpp
index 1416d6558..b4a9765f9 100644
--- a/lib/base/stacktrace.hpp
+++ b/lib/base/stacktrace.hpp
@@ -1,38 +1,31 @@
-/* Icinga 2 | (c) 2012 Icinga GmbH | GPLv2+ */
+/* Icinga 2 | (c) 2020 Icinga GmbH | GPLv2+ */
 
 #ifndef STACKTRACE_H
 #define STACKTRACE_H
 
-#include "base/i2-base.hpp"
-#include <iosfwd>
+#include <boost/stacktrace.hpp>
 
 namespace icinga
 {
 
 /**
- * A stacktrace.
+ * Formatter for `boost::stacktrace::stacktrace` objects
  *
- * @ingroup base
+ * This class wraps `boost::stacktrace::stacktrace` objects and provides an operator<<
+ * for printing them to an `std::ostream` in a custom format.
  */
-class StackTrace
-{
+class StackTraceFormatter {
 public:
-	StackTrace();
-#ifdef _WIN32
-	explicit StackTrace(PEXCEPTION_POINTERS exi);
-#endif /* _WIN32 */
-
-	void Print(std::ostream& fp, int ignoreFrames = 0) const;
-
-	static void StaticInitialize();
+	StackTraceFormatter(const boost::stacktrace::stacktrace &stack) : m_Stack(stack) {}
 
 private:
-	void *m_Frames[64];
-	int m_Count;
+	const boost::stacktrace::stacktrace &m_Stack;
+
+	friend std::ostream &operator<<(std::ostream &os, const StackTraceFormatter &f);
 };
 
-std::ostream& operator<<(std::ostream& stream, const StackTrace& trace);
+std::ostream& operator<<(std::ostream& os, const StackTraceFormatter &f);
 
 }
 
-#endif /* UTILITY_H */
+#endif /* STACKTRACE_H */
diff --git a/test/base-stacktrace.cpp b/test/base-stacktrace.cpp
index 349c2364a..f0b87e2cf 100644
--- a/test/base-stacktrace.cpp
+++ b/test/base-stacktrace.cpp
@@ -1,18 +1,72 @@
-/* Icinga 2 | (c) 2012 Icinga GmbH | GPLv2+ */
+/* Icinga 2 | (c) 2020 Icinga GmbH | GPLv2+ */
 
 #include "base/stacktrace.hpp"
 #include <BoostTestTargetConfig.h>
 
 using namespace icinga;
 
+
+/* If you are reading this, you are probably doing so because this test case just failed. This might happen as it
+ * heavily depends on platform and compiler behavior. There are two likely causes why this could break:
+ *
+ *  - Your compiler found new ways to optimize the functions that are called to create a stack, even though we tried
+ *    to disable optimizations using #pragmas for some compilers. If you know a way to disable (more) optimizations for
+ *    your compiler, you can try if this helps.
+ *
+ *  - Boost fails to resolve symbol names as we've already seen on some platforms. In this case, you can try again
+ *    passing the additional flag `-DICINGA2_STACKTRACE_USE_BACKTRACE_SYMBOLS=ON` to CMake and see if this helps.
+ *
+ *  In any case, please report a bug. If you run `make CTEST_OUTPUT_ON_FAILURE=1 test`, the stack trace in question
+ *  should be printed. If it looks somewhat meaningful, you can probably ignore a failure of this test case.
+ */
+
+#pragma GCC push_options
+#pragma GCC optimize ("O0")
+#pragma clang optimize off
+#ifdef _MSVC_VER
+#pragma optimize("", off)
+#endif /* _MSVC_VER */
+
 BOOST_AUTO_TEST_SUITE(base_stacktrace)
 
+[[gnu::noinline]]
+void stack_test_func_b()
+{
+	boost::stacktrace::stacktrace stack;
+	std::ostringstream obuf;
+	obuf << StackTraceFormatter(stack);
+	std::string result = obuf.str();
+	BOOST_CHECK_MESSAGE(!result.empty(), "stack trace must not be empty");
+	size_t pos_a = result.find("stack_test_func_a");
+	size_t pos_b = result.find("stack_test_func_b");
+	BOOST_CHECK_MESSAGE(pos_a != std::string::npos, "'stack_test_func_a' not found\n\n" << result);
+	BOOST_CHECK_MESSAGE(pos_b != std::string::npos, "'stack_test_func_b' not found\n\n" << result);
+	BOOST_CHECK_MESSAGE(pos_a > pos_b, "'stack_test_func_a' must appear after 'stack_test_func_b'\n\n" << result);
+}
+
+[[gnu::noinline]]
+void stack_test_func_a()
+{
+	boost::stacktrace::stacktrace stack;
+	std::ostringstream obuf;
+	obuf << StackTraceFormatter(stack);
+	std::string result = obuf.str();
+	BOOST_CHECK_MESSAGE(!result.empty(), "stack trace must not be empty");
+	size_t pos_a = result.find("stack_test_func_a");
+	BOOST_CHECK_MESSAGE(pos_a != std::string::npos, "'stack_test_func_a' not found\n\n" << result);
+
+	stack_test_func_b();
+}
+
 BOOST_AUTO_TEST_CASE(stacktrace)
 {
-	StackTrace st;
-	std::ostringstream obuf;
-	obuf << st;
-	BOOST_CHECK(obuf.str().size() > 0);
+	stack_test_func_a();
 }
 
 BOOST_AUTO_TEST_SUITE_END()
+
+#pragma GCC pop_options
+#pragma clang optimize on
+#ifdef _MSVC_VER
+#pragma optimize("", on)
+#endif /* _MSVC_VER */