diff --git a/src/plugins/cmakeprojectmanager/cmakeprojectimporter.cpp b/src/plugins/cmakeprojectmanager/cmakeprojectimporter.cpp
index 59f1d3796b0..e4e9ef90598 100644
--- a/src/plugins/cmakeprojectmanager/cmakeprojectimporter.cpp
+++ b/src/plugins/cmakeprojectmanager/cmakeprojectimporter.cpp
@@ -394,10 +394,7 @@ bool CMakeProjectImporter::matchKit(void *directoryData, const Kit *k) const
         if (!Utils::contains(allLanguages, [&tcd](const Id& language) {return language == tcd.language;}))
             continue;
         ToolChain *tc = ToolChainKitAspect::toolChain(k, tcd.language);
-        if (!tc
-            || !Utils::Environment::systemEnvironment()
-                    .isSameExecutable(tc->compilerCommand().toString(),
-                                      tcd.compilerPath.toString())) {
+        if (!tc || !tc->matchesCompilerCommand(tcd.compilerPath)) {
             return false;
         }
     }
diff --git a/src/plugins/projectexplorer/gcctoolchain.cpp b/src/plugins/projectexplorer/gcctoolchain.cpp
index 168062d154f..355ff2d7fc6 100644
--- a/src/plugins/projectexplorer/gcctoolchain.cpp
+++ b/src/plugins/projectexplorer/gcctoolchain.cpp
@@ -1580,6 +1580,27 @@ ClangToolChain::~ClangToolChain()
     QObject::disconnect(m_mingwToolchainAddedConnection);
 }
 
+bool ClangToolChain::matchesCompilerCommand(const Utils::FilePath &command,
+                                            const Utils::Environment &env) const
+{
+    if (!m_resolvedCompilerCommand) {
+        m_resolvedCompilerCommand = FilePath();
+        if (HostOsInfo::isMacHost()
+            && compilerCommand().parentDir() == FilePath::fromString("/usr/bin")) {
+            std::unique_ptr<QtcProcess> xcrun(new QtcProcess);
+            xcrun->setCommand({"/usr/bin/xcrun", {"-f", compilerCommand().fileName()}});
+            xcrun->runBlocking();
+            const FilePath output = FilePath::fromString(xcrun->stdOut().trimmed());
+            if (output.isExecutableFile() && output != compilerCommand())
+                m_resolvedCompilerCommand = output;
+        }
+    }
+    if (!m_resolvedCompilerCommand->isEmpty()
+        && env.isSameExecutable(m_resolvedCompilerCommand->toString(), command.toString()))
+        return true;
+    return GccToolChain::matchesCompilerCommand(command, env);
+}
+
 static FilePath mingwAwareMakeCommand(const Environment &environment)
 {
     const QStringList makes
diff --git a/src/plugins/projectexplorer/gcctoolchain.h b/src/plugins/projectexplorer/gcctoolchain.h
index 7bd83d0a1b2..bad26674e23 100644
--- a/src/plugins/projectexplorer/gcctoolchain.h
+++ b/src/plugins/projectexplorer/gcctoolchain.h
@@ -33,6 +33,7 @@
 #include "headerpath.h"
 
 #include <utils/fileutils.h>
+#include <utils/optional.h>
 
 #include <functional>
 #include <memory>
@@ -211,6 +212,10 @@ public:
     explicit ClangToolChain(Utils::Id typeId);
     ~ClangToolChain() override;
 
+    bool matchesCompilerCommand(
+        const Utils::FilePath &command,
+        const Utils::Environment &env = Utils::Environment::systemEnvironment()) const override;
+
     Utils::FilePath makeCommand(const Utils::Environment &environment) const override;
 
     Utils::LanguageExtensions languageExtensions(const QStringList &cxxflags) const override;
@@ -237,6 +242,9 @@ protected:
     void syncAutodetectedWithParentToolchains();
 
 private:
+    // "resolved" on macOS from /usr/bin/clang(++) etc to <DeveloperDir>/usr/bin/clang(++)
+    // which is used for comparison with matchesCompileCommand
+    mutable Utils::optional<Utils::FilePath> m_resolvedCompilerCommand;
     QByteArray m_parentToolChainId;
     QMetaObject::Connection m_mingwToolchainAddedConnection;
     QMetaObject::Connection m_thisToolchainRemovedConnection;
diff --git a/src/plugins/projectexplorer/projectimporter.cpp b/src/plugins/projectexplorer/projectimporter.cpp
index 2db6dafa2b6..e51aaa2c968 100644
--- a/src/plugins/projectexplorer/projectimporter.cpp
+++ b/src/plugins/projectexplorer/projectimporter.cpp
@@ -414,9 +414,7 @@ ProjectImporter::findOrCreateToolChains(const ToolChainDescription &tcd) const
 {
     ToolChainData result;
     result.tcs = ToolChainManager::toolchains([&tcd](const ToolChain *tc) {
-        return tc->language() == tcd.language &&
-               Utils::Environment::systemEnvironment().isSameExecutable(
-                    tc->compilerCommand().toString(), tcd.compilerPath.toString());
+        return tc->language() == tcd.language && tc->matchesCompilerCommand(tcd.compilerPath);
     });
     for (const ToolChain *tc : qAsConst(result.tcs)) {
         const QByteArray tcId = tc->id();
diff --git a/src/plugins/projectexplorer/toolchain.cpp b/src/plugins/projectexplorer/toolchain.cpp
index f36ce9414b6..32d39fc0806 100644
--- a/src/plugins/projectexplorer/toolchain.cpp
+++ b/src/plugins/projectexplorer/toolchain.cpp
@@ -343,6 +343,11 @@ void ToolChain::setCompilerCommand(const FilePath &command)
     toolChainUpdated();
 }
 
+bool ToolChain::matchesCompilerCommand(const Utils::FilePath &command, const Environment &env) const
+{
+    return env.isSameExecutable(compilerCommand().toString(), command.toString());
+}
+
 void ToolChain::setCompilerCommandKey(const QString &commandKey)
 {
     d->m_compilerCommandKey = commandKey;
diff --git a/src/plugins/projectexplorer/toolchain.h b/src/plugins/projectexplorer/toolchain.h
index 2e41313f2ec..6a3ced00535 100644
--- a/src/plugins/projectexplorer/toolchain.h
+++ b/src/plugins/projectexplorer/toolchain.h
@@ -156,6 +156,9 @@ public:
 
     virtual Utils::FilePath compilerCommand() const; // FIXME: De-virtualize.
     void setCompilerCommand(const Utils::FilePath &command);
+    virtual bool matchesCompilerCommand(
+        const Utils::FilePath &command,
+        const Utils::Environment &env = Utils::Environment::systemEnvironment()) const;
 
     virtual QList<Utils::OutputLineParser *> createOutputParsers() const = 0;
 
diff --git a/src/plugins/qmakeprojectmanager/qmakeproject.cpp b/src/plugins/qmakeprojectmanager/qmakeproject.cpp
index c77f468ae23..bff8df79024 100644
--- a/src/plugins/qmakeprojectmanager/qmakeproject.cpp
+++ b/src/plugins/qmakeprojectmanager/qmakeproject.cpp
@@ -1390,7 +1390,7 @@ void QmakeBuildSystem::testToolChain(ToolChain *tc, const FilePath &path) const
     const Utils::FilePath expected = tc->compilerCommand();
     Environment env = buildConfiguration()->environment();
 
-    if (env.isSameExecutable(path.toString(), expected.toString()))
+    if (tc->matchesCompilerCommand(expected, env))
         return;
     const QPair<Utils::FilePath, Utils::FilePath> pair = qMakePair(expected, path);
     if (m_toolChainWarnings.contains(pair))