diff --git a/Headers/DebugServer2/GDBRemote/Mixins/FileOperationsMixin.h b/Headers/DebugServer2/GDBRemote/Mixins/FileOperationsMixin.h
index 522fb363..dbe12616 100644
--- a/Headers/DebugServer2/GDBRemote/Mixins/FileOperationsMixin.h
+++ b/Headers/DebugServer2/GDBRemote/Mixins/FileOperationsMixin.h
@@ -30,6 +30,17 @@ template <typename T> class FileOperationsMixin : public T {
   explicit FileOperationsMixin(Args &&... args)
       : T(std::forward<Args>(args)...) {}
 
+private:
+  // vFile paths are frequently relative (e.g. a bare filename an inferior
+  // writes into its own working directory); unlike qPlatform_shell, the
+  // vFile packets carry no separate working-directory field, so ds2 has to
+  // apply the platform session's own configured working directory itself.
+  // This has to stay session-local rather than mutating ds2's actual
+  // process cwd: platform mode serves each connected client on its own
+  // thread with its own session (see PlatformMain in Sources/main.cpp), and
+  // the process cwd is shared state across all of them.
+  std::string resolvePath(Session &session, std::string const &path) const;
+
 protected:
   ErrorCode onFileOpen(Session &session, std::string const &path,
                        OpenFlags flags, uint32_t mode, int &fd) override;
diff --git a/Sources/GDBRemote/Mixins/FileOperationsMixin.hpp b/Sources/GDBRemote/Mixins/FileOperationsMixin.hpp
index c067d7a3..96f5817f 100644
--- a/Sources/GDBRemote/Mixins/FileOperationsMixin.hpp
+++ b/Sources/GDBRemote/Mixins/FileOperationsMixin.hpp
@@ -13,6 +13,7 @@
 #include "DebugServer2/GDBRemote/Mixins/FileOperationsMixin.h"
 #include "DebugServer2/Host/Platform.h"
 
+#include <filesystem>
 #include <iomanip>
 #include <sstream>
 
@@ -23,12 +24,30 @@ namespace ds2 {
 namespace GDBRemote {
 
 template <typename T>
-ErrorCode FileOperationsMixin<T>::onFileOpen(Session &, std::string const &path,
+std::string FileOperationsMixin<T>::resolvePath(Session &session,
+                                                 std::string const &path) const {
+  if (std::filesystem::path(path).is_absolute()) {
+    return path;
+  }
+
+  std::string workingDirectory;
+  if (this->onQueryWorkingDirectory(session, workingDirectory) != kSuccess ||
+      workingDirectory.empty()) {
+    return path;
+  }
+
+  // onSetWorkingDirectory canonicalizes to an absolute path before storing
+  // it, so this join always yields an absolute result.
+  return (std::filesystem::path(workingDirectory) / path).string();
+}
+
+template <typename T>
+ErrorCode FileOperationsMixin<T>::onFileOpen(Session &session, std::string const &path,
                                              OpenFlags flags, uint32_t mode,
                                              int &fd) {
   static int fileIdx = 0;
 
-  Host::File file(path, flags, mode);
+  Host::File file(resolvePath(session, path), flags, mode);
   if (!file.valid()) {
     return file.lastError();
   }
@@ -76,29 +95,30 @@ ErrorCode FileOperationsMixin<T>::onFileWrite(Session &session, int fd,
 }
 
 template <typename T>
-ErrorCode FileOperationsMixin<T>::onFileCreateDirectory(Session &,
+ErrorCode FileOperationsMixin<T>::onFileCreateDirectory(Session &session,
                                                         std::string const &path,
                                                         uint32_t flags) {
-  return Host::File::createDirectory(path, flags);
+  return Host::File::createDirectory(resolvePath(session, path), flags);
 }
 
 template <typename T>
-ErrorCode FileOperationsMixin<T>::onFileExists(Session &,
+ErrorCode FileOperationsMixin<T>::onFileExists(Session &session,
                                                std::string const &path) {
-  return Host::Platform::IsFilePresent(path) ? kSuccess : kErrorNotFound;
+  return Host::Platform::IsFilePresent(resolvePath(session, path)) ? kSuccess
+                                                                    : kErrorNotFound;
 }
 
 template <typename T>
 ErrorCode FileOperationsMixin<T>::onFileGetSize(Session &session, std::string const &path,
                         uint64_t &size){
-  return Host::File::fileSize(path, size);
+  return Host::File::fileSize(resolvePath(session, path), size);
 }
 
 template <typename T>
 ErrorCode FileOperationsMixin<T>::onFileGetMode(Session &session,
                                                 std::string const &path,
                                                 uint32_t &mode) const {
-  return Host::File::fileMode(path, mode);
+  return Host::File::fileMode(resolvePath(session, path), mode);
 }
 
 template <typename T>
@@ -114,14 +134,14 @@ ErrorCode FileOperationsMixin<T>::onFileFstat(Session &session, int fd,
 template <typename T>
 ErrorCode FileOperationsMixin<T>::onFileRemove(Session &session,
                                                std::string const &path) {
-  return Host::File::unlink(path);
+  return Host::File::unlink(resolvePath(session, path));
 }
 
 template <typename T>
 ErrorCode FileOperationsMixin<T>::onFileSetPermissions(Session &session,
                                                        std::string const &path,
                                                        uint32_t mode) {
-  return Host::File::chmod(path, mode);
+  return Host::File::chmod(resolvePath(session, path), mode);
 }
 
 template <typename T>
diff --git a/Sources/GDBRemote/Mixins/ProcessLaunchMixin.hpp b/Sources/GDBRemote/Mixins/ProcessLaunchMixin.hpp
index 5a78fd14..00b5809d 100644
--- a/Sources/GDBRemote/Mixins/ProcessLaunchMixin.hpp
+++ b/Sources/GDBRemote/Mixins/ProcessLaunchMixin.hpp
@@ -13,6 +13,7 @@
 #include "DebugServer2/GDBRemote/Mixins/ProcessLaunchMixin.h"
 
 #include <algorithm>
+#include <filesystem>
 
 namespace ds2 {
 namespace GDBRemote {
@@ -35,7 +36,23 @@ template <typename T>
 ErrorCode
 ProcessLaunchMixin<T>::onSetWorkingDirectory(Session &,
                                              std::string const &path) {
-  _workingDirectory = path;
+  // ds2 serves each platform client on its own thread with its own session
+  // (see PlatformMain in Sources/main.cpp), so the working directory has to
+  // stay session-local state rather than ds2's actual process cwd, which is
+  // shared by every concurrently-connected client.
+  //
+  // Canonicalize to an absolute path here, once, rather than storing
+  // whatever the client sent verbatim: a relative path only means
+  // something relative to ds2's own starting directory (there is nothing
+  // else for it to be relative to, since ds2's cwd never changes), and
+  // resolving it eagerly means every later consumer of _workingDirectory
+  // (vFile path resolution, ProcessSpawner) can treat it as absolute
+  // without redoing this resolution or applying it a second time.
+  std::filesystem::path resolved(path);
+  if (!resolved.is_absolute())
+    resolved = std::filesystem::path(Platform::GetWorkingDirectory()) / resolved;
+
+  _workingDirectory = resolved.string();
   return kSuccess;
 }