diff --git a/pkg/dartdev/lib/src/sdk.dart b/pkg/dartdev/lib/src/sdk.dart
index a67a7c55dc3..9ce1ed12810 100644
--- a/pkg/dartdev/lib/src/sdk.dart
+++ b/pkg/dartdev/lib/src/sdk.dart
@@ -30,7 +30,7 @@ class Sdk {
   // Assume that we want to use the same Dart executable that we used to spawn
   // DartDev. We should be able to run programs with out/ReleaseX64/dart even
   // if the SDK isn't completely built.
-  String get dart => Platform.resolvedExecutable;
+  String get dart => Platform.executable;
 
   String get dartAotRuntime => _runFromBuildRoot
       ? path.absolute(
@@ -149,22 +149,37 @@ class Sdk {
 
   static Sdk _createSingleton() {
     // Find SDK path.
+    (String, bool)? trySDKPath(String executablePath) {
+      // The common case, and how cli_util.dart computes the Dart SDK directory,
+      // [path.dirname] called twice on Platform.executable. We confirm by
+      // asserting that the directory `./bin/snapshots/` exists in this directory:
+      var sdkPath = path.absolute(path.dirname(path.dirname(executablePath)));
+      var snapshotsDir = path.join(sdkPath, 'bin', 'snapshots');
+      var runFromBuildRoot = false;
+      if (!Directory(snapshotsDir).existsSync()) {
+        // This is the less common case where the user is in
+        // the checked out Dart SDK, and is executing `dart` via:
+        // ./out/ReleaseX64/dart ... or in google3.
+        sdkPath = path.absolute(path.dirname(executablePath));
+        snapshotsDir = sdkPath;
+        runFromBuildRoot = true;
+      }
 
-    // The common case, and how cli_util.dart computes the Dart SDK directory,
-    // [path.dirname] called twice on Platform.resolvedExecutable. We confirm by
-    // asserting that the directory `./bin/snapshots/` exists in this directory:
-    var sdkPath =
-        path.absolute(path.dirname(path.dirname(Platform.resolvedExecutable)));
-    var snapshotsDir = path.join(sdkPath, 'bin', 'snapshots');
-    var runFromBuildRoot = false;
-    if (!Directory(snapshotsDir).existsSync()) {
-      // This is the less common case where the user is in
-      // the checked out Dart SDK, and is executing `dart` via:
-      // ./out/ReleaseX64/dart ... or in google3.
-      sdkPath = path.absolute(path.dirname(Platform.resolvedExecutable));
-      runFromBuildRoot = true;
+      // Try to locate the DartDev snapshot to determine if we're able to find
+      // the SDK snapshots with this SDK path. This is meant to handle
+      // non-standard SDK layouts that can involve symlinks (e.g., Brew
+      // installations, google3 tests, etc).
+      if (!File(path.join(snapshotsDir, 'dartdev.dart.snapshot'))
+          .existsSync()) {
+        return null;
+      }
+      return (sdkPath, runFromBuildRoot);
     }
 
+    final (sdkPath, runFromBuildRoot) =
+        trySDKPath(Platform.resolvedExecutable) ??
+            trySDKPath(Platform.executable)!;
+
     // Defer to [Runtime] for the version.
     var version = Runtime.runtime.version;
 
diff --git a/runtime/bin/dartdev_isolate.cc b/runtime/bin/dartdev_isolate.cc
index 7116b7dad56..d00a10e9236 100644
--- a/runtime/bin/dartdev_isolate.cc
+++ b/runtime/bin/dartdev_isolate.cc
@@ -80,25 +80,37 @@ bool DartDevIsolate::ShouldParseCommand(const char* script_uri) {
 }
 
 CStringUniquePtr DartDevIsolate::TryResolveArtifactPath(const char* filename) {
-  // |dir_prefix| includes the last path separator.
-  auto dir_prefix = EXEUtils::GetDirectoryPrefixFromExeName();
+  auto try_resolve_path = [&](CStringUniquePtr dir_prefix) {
+    // First assume we're in dart-sdk/bin.
+    char* snapshot_path =
+        Utils::SCreate("%ssnapshots/%s", dir_prefix.get(), filename);
+    if (File::Exists(nullptr, snapshot_path)) {
+      return CStringUniquePtr(snapshot_path);
+    }
+    free(snapshot_path);
 
-  // First assume we're in dart-sdk/bin.
-  char* snapshot_path =
-      Utils::SCreate("%ssnapshots/%s", dir_prefix.get(), filename);
-  if (File::Exists(nullptr, snapshot_path)) {
-    return CStringUniquePtr(snapshot_path);
-  }
-  free(snapshot_path);
+    // If we're not in dart-sdk/bin, we might be in one of the $SDK/out/*
+    // directories. Try to use a snapshot from a previously built SDK.
+    snapshot_path = Utils::SCreate("%s%s", dir_prefix.get(), filename);
+    if (File::Exists(nullptr, snapshot_path)) {
+      return CStringUniquePtr(snapshot_path);
+    }
+    free(snapshot_path);
+    return CStringUniquePtr(nullptr);
+  };
 
-  // If we're not in dart-sdk/bin, we might be in one of the $SDK/out/*
-  // directories. Try to use a snapshot from a previously built SDK.
-  snapshot_path = Utils::SCreate("%s%s", dir_prefix.get(), filename);
-  if (File::Exists(nullptr, snapshot_path)) {
-    return CStringUniquePtr(snapshot_path);
+  // Try to find the artifact using the resolved EXE path first. This can fail
+  // if the Dart SDK file structure is faked using symlinks and the actual
+  // artifacts are spread across directories on the file system (e.g., some
+  // google3 execution environments).
+  auto result =
+      try_resolve_path(EXEUtils::GetDirectoryPrefixFromResolvedExeName());
+  if (result == nullptr) {
+    result =
+        try_resolve_path(EXEUtils::GetDirectoryPrefixFromUnresolvedExeName());
   }
-  free(snapshot_path);
-  return CStringUniquePtr(nullptr);
+
+  return result;
 }
 
 CStringUniquePtr DartDevIsolate::TryResolveDartDevSnapshotPath() {
diff --git a/runtime/bin/dfe.cc b/runtime/bin/dfe.cc
index 898c29562c0..12e2546bba2 100644
--- a/runtime/bin/dfe.cc
+++ b/runtime/bin/dfe.cc
@@ -101,7 +101,7 @@ void DFE::InitKernelServiceAndPlatformDills() {
   }
 
   // |dir_prefix| includes the last path separator.
-  auto dir_prefix = EXEUtils::GetDirectoryPrefixFromExeName();
+  auto dir_prefix = EXEUtils::GetDirectoryPrefixFromResolvedExeName();
 
   // Look for the frontend snapshot next to the executable.
   frontend_filename_ =
diff --git a/runtime/bin/exe_utils.cc b/runtime/bin/exe_utils.cc
index 3b8d6fa50e1..2e4049ea322 100644
--- a/runtime/bin/exe_utils.cc
+++ b/runtime/bin/exe_utils.cc
@@ -65,7 +65,7 @@ static const char* GetFileNameFromPath(const char* path) {
   return path;
 }
 
-CStringUniquePtr EXEUtils::GetDirectoryPrefixFromExeName() {
+CStringUniquePtr EXEUtils::GetDirectoryPrefixFromResolvedExeName() {
   const char* name = nullptr;
   const int kTargetSize = PATH_MAX;
   char target[kTargetSize];
@@ -119,6 +119,12 @@ CStringUniquePtr EXEUtils::GetDirectoryPrefixFromExeName() {
   return CStringUniquePtr(result == nullptr ? Utils::StrDup("") : result);
 }
 
+CStringUniquePtr EXEUtils::GetDirectoryPrefixFromUnresolvedExeName() {
+  const char* exe = Platform::GetExecutableName();
+  return CStringUniquePtr(exe == nullptr ? nullptr
+                                         : GetDirectoryFromPath(exe, nullptr));
+}
+
 #if !defined(DART_HOST_OS_WINDOWS)
 void EXEUtils::LoadDartProfilerSymbols(const char* argv0) {
   char* path = reinterpret_cast<char*>(malloc(PATH_MAX + 5));
diff --git a/runtime/bin/exe_utils.h b/runtime/bin/exe_utils.h
index 1540cd53287..b2fba1bcc62 100644
--- a/runtime/bin/exe_utils.h
+++ b/runtime/bin/exe_utils.h
@@ -17,8 +17,15 @@ namespace bin {
 
 class EXEUtils {
  public:
-  // Returns the path to the directory the current executable resides in.
-  static CStringUniquePtr GetDirectoryPrefixFromExeName();
+  // Returns the resolved path to the directory the current executable resides
+  // in.
+  static CStringUniquePtr GetDirectoryPrefixFromResolvedExeName();
+
+  // Returns the path to the directory the current executable resides
+  // in without following symlinks.
+  //
+  // Returns null if Platform::GetExecutableName() returns null.
+  static CStringUniquePtr GetDirectoryPrefixFromUnresolvedExeName();
 
 #if !defined(DART_HOST_OS_WINDOWS)
   // Loads a compact symbolization table from "$exepath.sym" that is used by the