diff --git a/test/CMakeLists.txt b/test/CMakeLists.txt
index cc7a61bae..2fcea2269 100644
--- a/test/CMakeLists.txt
+++ b/test/CMakeLists.txt
@@ -73,6 +73,8 @@ set(libsolidity_sources
     libsolidity/Assembly.cpp
     libsolidity/ASTJSONTest.cpp
     libsolidity/ASTJSONTest.h
+    libsolidity/ASTJSONPropertyTest.cpp
+    libsolidity/ASTJSONPropertyTest.h
     libsolidity/ErrorCheck.cpp
     libsolidity/ErrorCheck.h
     libsolidity/GasCosts.cpp
diff --git a/test/InteractiveTests.h b/test/InteractiveTests.h
index d359a815a..7d1f6192e 100644
--- a/test/InteractiveTests.h
+++ b/test/InteractiveTests.h
@@ -21,6 +21,7 @@
 #include <test/TestCase.h>
 #include <test/libsolidity/ABIJsonTest.h>
 #include <test/libsolidity/ASTJSONTest.h>
+#include <test/libsolidity/ASTJSONPropertyTest.h>
 #include <test/libsolidity/GasTest.h>
 #include <test/libsolidity/MemoryGuardTest.h>
 #include <test/libsolidity/SyntaxTest.h>
@@ -72,6 +73,7 @@ Testsuite const g_interactiveTestsuites[] = {
 	{"Error Recovery",         "libsolidity", "errorRecoveryTests",    false, false, &SyntaxTest::createErrorRecovery},
 	{"Semantic",               "libsolidity", "semanticTests",         false, true,  &SemanticTest::create},
 	{"JSON AST",               "libsolidity", "ASTJSON",               false, false, &ASTJSONTest::create},
+	{"JSON AST Properties",    "libsolidity", "ASTJSONProperties",     false, false, &ASTJSONPropertyTest::create},
 	{"JSON ABI",               "libsolidity", "ABIJson",               false, false, &ABIJsonTest::create},
 	{"SMT Checker",            "libsolidity", "smtCheckerTests",       true,  false, &SMTCheckerTest::create},
 	{"Gas Estimates",          "libsolidity", "gasTests",              false, false, &GasTest::create},
diff --git a/test/libsolidity/ASTJSONProperties/simple_for_loop.sol b/test/libsolidity/ASTJSONProperties/simple_for_loop.sol
new file mode 100644
index 000000000..c221542da
--- /dev/null
+++ b/test/libsolidity/ASTJSONProperties/simple_for_loop.sol
@@ -0,0 +1,16 @@
+function f() pure {
+    /// @custom:test { "isSimpleCounterLoop": true }
+    for (uint i = 0; i < 32; ++i) {
+    }
+    /// @custom:test { "isSimpleCounterLoop": true }
+    for (uint i = 0; i < 32; i++) {
+    }
+    /// @custom:test { "isSimpleCounterLoop": true }
+    for (uint i = 0; i < i; ++i) {
+    }
+    /// @custom:test { "isSimpleCounterLoop": false }
+    for (uint i = 0; 0 < i; ++i) {
+    }
+}
+
+// ----
diff --git a/test/libsolidity/ASTJSONPropertyTest.cpp b/test/libsolidity/ASTJSONPropertyTest.cpp
new file mode 100644
index 000000000..0eba92c73
--- /dev/null
+++ b/test/libsolidity/ASTJSONPropertyTest.cpp
@@ -0,0 +1,205 @@
+/*
+	This file is part of solidity.
+
+	solidity is free software: you can redistribute it and/or modify
+	it under the terms of the GNU General Public License as published by
+	the Free Software Foundation, either version 3 of the License, or
+	(at your option) any later version.
+
+	solidity is distributed in the hope that it will be useful,
+	but WITHOUT ANY WARRANTY; without even the implied warranty of
+	MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+	GNU General Public License for more details.
+
+	You should have received a copy of the GNU General Public License
+	along with solidity.  If not, see <http://www.gnu.org/licenses/>.
+*/
+// SPDX-License-Identifier: GPL-3.0
+
+#include <liblangutil/SourceReferenceFormatter.h>
+#include <libsolidity/ast/ASTJsonExporter.h>
+#include <libsolutil/AnsiColorized.h>
+#include <libsolutil/CommonIO.h>
+#include <libsolutil/JSON.h>
+
+#include <test/Common.h>
+#include <test/libsolidity/ASTJSONPropertyTest.h>
+
+#include <boost/algorithm/string.hpp>
+#include <boost/algorithm/string/predicate.hpp>
+#include <boost/algorithm/string/replace.hpp>
+#include <boost/algorithm/string/trim.hpp>
+#include <boost/test/unit_test.hpp>
+#include <boost/throw_exception.hpp>
+
+#include <fstream>
+#include <memory>
+#include <stdexcept>
+
+using namespace solidity::langutil;
+using namespace solidity::frontend;
+using namespace solidity::frontend::test;
+using namespace solidity::util::formatting;
+using namespace solidity::util;
+using namespace solidity;
+using namespace std;
+namespace fs = boost::filesystem;
+using namespace boost::unit_test;
+
+namespace
+{
+
+string const sourceDelimiter("==== Source: ");
+
+}
+
+void ASTJSONPropertyTest::fillSources(string const& _filename)
+{
+	ifstream file(_filename);
+	if (!file)
+		BOOST_THROW_EXCEPTION(runtime_error("Cannot open test contract: \"" + _filename + "\"."));
+	file.exceptions(ios::badbit);
+
+	string sourceName;
+	string source;
+	string line;
+	string const delimiter("// ----");
+	while (getline(file, line))
+	{
+		if (boost::algorithm::starts_with(line, sourceDelimiter))
+		{
+			if (!sourceName.empty())
+				m_sources.emplace_back(sourceName, source);
+
+			sourceName = line.substr(
+				sourceDelimiter.size(),
+				line.size() - " ===="s.size() - sourceDelimiter.size()
+			);
+			source = string();
+		}
+		else if (!line.empty() && !boost::algorithm::starts_with(line, delimiter))
+			source += line + "\n";
+	}
+	m_sources.emplace_back(sourceName.empty() ? "a" : sourceName, source);
+	file.close();
+}
+
+ASTJSONPropertyTest::ASTJSONPropertyTest(string const& _filename)
+{
+	if (!boost::algorithm::ends_with(_filename, ".sol"))
+		BOOST_THROW_EXCEPTION(runtime_error("Invalid test contract file name: \"" + _filename + "\"."));
+
+	fillSources(_filename);
+}
+
+TestCase::TestResult ASTJSONPropertyTest::run(ostream& _stream, string const& _linePrefix, bool const _formatted)
+{
+	CompilerStack c;
+
+	StringMap sources;
+	map<string, unsigned> sourceIndices;
+	for (size_t i = 0; i < m_sources.size(); i++)
+	{
+		sources[m_sources[i].first] = m_sources[i].second;
+		sourceIndices[m_sources[i].first] = static_cast<unsigned>(i + 1);
+	}
+
+	c.reset();
+	c.setSources(sources);
+	c.setEVMVersion(solidity::test::CommonOptions::get().evmVersion());
+
+	if (!c.parseAndAnalyze())
+		return TestResult::FatalError;
+
+	return runTest(
+		sourceIndices,
+		c,
+		_stream,
+		_linePrefix,
+		_formatted
+	) ? TestResult::Success : TestResult::Failure;
+}
+
+bool ASTJSONPropertyTest::checkASTProperty(std::string _property, Json::Value const& _node)
+{
+	Json::Value properties;
+	std::string error;
+	if (!jsonParseStrict(_property, properties, &error))
+		BOOST_THROW_EXCEPTION(runtime_error("Invalid test property: \"" + _property + "\": " + error));
+
+	for (auto propertyName: properties.getMemberNames())
+	{
+		if (_node[propertyName] != properties[propertyName])
+		{
+			std::cout << jsonCompactPrint(_node[propertyName]) << " != " << jsonCompactPrint(properties[propertyName]) << std::endl;
+			return false;
+		}
+	}
+
+	return true;
+}
+
+bool ASTJSONPropertyTest::runTest(
+	map<string, unsigned> const& _sourceIndices,
+	CompilerStack& _compiler,
+	ostream& /*_stream*/,
+	string const& /*_linePrefix*/,
+	bool const /*_formatted*/
+)
+{
+	for (size_t i = 0; i < m_sources.size(); i++)
+	{
+		auto jsonAST = ASTJsonExporter(_compiler.state(), _sourceIndices).toJson(_compiler.ast(m_sources[i].first));
+
+		auto walkAST = [this](Json::Value const& _node, auto _recurse) -> bool {
+			if (_node.type() == Json::ValueType::objectValue && _node.isMember("documentation"))
+			{
+				std::string docString = _node.get("documentation", {}).asString();
+				static constexpr std::string_view testMarker = "@custom:test ";
+				if (boost::starts_with(docString, testMarker))
+					if (!checkASTProperty(docString.substr(testMarker.size()), _node))
+						return false;
+			}
+			for (auto const& member: _node)
+				if (!_recurse(member, _recurse))
+					return false;
+			return true;
+		};
+
+		if (!walkAST(jsonAST, walkAST))
+			return false;
+	}
+
+	return true;
+}
+
+void ASTJSONPropertyTest::printSource(ostream& _stream, string const& _linePrefix, bool const) const
+{
+	for (auto const& source: m_sources)
+	{
+		if (m_sources.size() > 1 || source.first != "a")
+			_stream << _linePrefix << sourceDelimiter << source.first << " ====" << endl << endl;
+		stringstream stream(source.second);
+		string line;
+		while (getline(stream, line))
+			_stream << _linePrefix << line << endl;
+		_stream << endl;
+	}
+}
+
+void ASTJSONPropertyTest::printUpdatedExpectations(std::ostream&, std::string const&) const
+{
+}
+
+void ASTJSONPropertyTest::updateExpectation(string const& _filename, string const& _expectation, string const& _variant) const
+{
+	ofstream file(_filename.c_str());
+	if (!file) BOOST_THROW_EXCEPTION(runtime_error("Cannot write " + _variant + "AST expectation to \"" + _filename + "\"."));
+	file.exceptions(ios::badbit);
+
+	string replacedResult = _expectation;
+
+	file << replacedResult;
+	file.flush();
+	file.close();
+}
diff --git a/test/libsolidity/ASTJSONPropertyTest.h b/test/libsolidity/ASTJSONPropertyTest.h
new file mode 100644
index 000000000..9c90a3820
--- /dev/null
+++ b/test/libsolidity/ASTJSONPropertyTest.h
@@ -0,0 +1,71 @@
+/*
+	This file is part of solidity.
+
+	solidity is free software: you can redistribute it and/or modify
+	it under the terms of the GNU General Public License as published by
+	the Free Software Foundation, either version 3 of the License, or
+	(at your option) any later version.
+
+	solidity is distributed in the hope that it will be useful,
+	but WITHOUT ANY WARRANTY; without even the implied warranty of
+	MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+	GNU General Public License for more details.
+
+	You should have received a copy of the GNU General Public License
+	along with solidity.  If not, see <http://www.gnu.org/licenses/>.
+*/
+// SPDX-License-Identifier: GPL-3.0
+
+#pragma once
+
+#include <libsolutil/AnsiColorized.h>
+#include <libsolidity/interface/CompilerStack.h>
+#include <test/TestCase.h>
+
+#include <iosfwd>
+#include <string>
+#include <vector>
+#include <utility>
+
+namespace solidity::frontend
+{
+class CompilerStack;
+}
+
+namespace solidity::frontend::test
+{
+
+class ASTJSONPropertyTest: public TestCase
+{
+public:
+	static std::unique_ptr<TestCase> create(Config const& _config)
+	{
+		return std::make_unique<ASTJSONPropertyTest>(_config.filename);
+	}
+	ASTJSONPropertyTest(std::string const& _filename);
+
+	TestResult run(std::ostream& _stream, std::string const& _linePrefix = "", bool const _formatted = false) override;
+
+	void printSource(std::ostream& _stream, std::string const& _linePrefix = "", bool const _formatted = false) const override;
+	void printUpdatedExpectations(std::ostream& _stream, std::string const& _linePrefix) const override;
+private:
+	bool checkASTProperty(std::string _property, Json::Value const& _node);
+	bool runTest(
+		std::map<std::string, unsigned> const& _sourceIndices,
+		CompilerStack& _compiler,
+		std::ostream& _stream,
+		std::string const& _linePrefix = "",
+		bool const _formatted = false
+	);
+	void updateExpectation(
+		std::string const& _filename,
+		std::string const& _expectation,
+		std::string const& _variant
+	) const;
+
+	void fillSources(std::string const& _filename);
+
+	std::vector<std::pair<std::string, std::string>> m_sources;
+};
+
+}
diff --git a/test/tools/CMakeLists.txt b/test/tools/CMakeLists.txt
index 5971341ec..a2a755f78 100644
--- a/test/tools/CMakeLists.txt
+++ b/test/tools/CMakeLists.txt
@@ -31,6 +31,7 @@ add_executable(isoltest
 	../ExecutionFramework.cpp
 	../libsolidity/ABIJsonTest.cpp
 	../libsolidity/ASTJSONTest.cpp
+	../libsolidity/ASTJSONPropertyTest.cpp
 	../libsolidity/SMTCheckerTest.cpp
 	../libyul/Common.cpp
 	../libyul/ControlFlowGraphTest.cpp