diff --git a/lldb/source/Utility/TildeExpressionResolver.cpp b/lldb/source/Utility/TildeExpressionResolver.cpp
--- a/lldb/source/Utility/TildeExpressionResolver.cpp
+++ b/lldb/source/Utility/TildeExpressionResolver.cpp
@@ -11,6 +11,7 @@
 #include <cassert>
 #include <system_error>
 
+#include "lldb/Utility/ConstString.h"
 #include "llvm/ADT/STLExtras.h"
 #include "llvm/ADT/SmallVector.h"
 #include "llvm/Support/FileSystem.h"
@@ -75,6 +76,7 @@
 
 bool TildeExpressionResolver::ResolveFullPath(
     StringRef Expr, llvm::SmallVectorImpl<char> &Output) {
+  static std::vector<std::tuple<ConstString, std::string>> g_tildes_expanded;
   if (!Expr.startswith("~")) {
     Output.assign(Expr.begin(), Expr.end());
     return false;
@@ -84,11 +86,27 @@
   StringRef Left =
       Expr.take_until([](char c) { return path::is_separator(c); });
 
-  if (!ResolveExact(Left, Output)) {
-    Output.assign(Expr.begin(), Expr.end());
-    return false;
+  ConstString tilde_name(Left);
+  std::string expanded_path;
+  for (const auto &it : g_tildes_expanded) {
+    if (std::get<0>(it) == tilde_name) {
+      expanded_path = std::get<1>(it);
+      break;
+    }
   }
 
-  Output.append(Expr.begin() + Left.size(), Expr.end());
+  if (expanded_path.empty()) {
+    if (!ResolveExact(Left, Output)) {
+      Output.assign(Expr.begin(), Expr.end());
+      return false;
+    }
+    expanded_path = std::string(Output.data(), Output.size());
+    g_tildes_expanded.push_back(
+        std::tuple<ConstString, std::string>(tilde_name, expanded_path));
+  } else {
+    StringRef expanded_strref(expanded_path);
+    Output.assign(expanded_path.begin(), expanded_path.end());
+  }
+  Output.append(Expr.begin() + tilde_name.GetLength(), Expr.end());
   return true;
 }