diff --git a/Source/Core/Common/FileUtil.cpp b/Source/Core/Common/FileUtil.cpp
index 742fbb546f..d84b725e70 100644
--- a/Source/Core/Common/FileUtil.cpp
+++ b/Source/Core/Common/FileUtil.cpp
@@ -932,7 +932,7 @@ static void RebuildUserDirectories(unsigned int dir_index)
   {
   case D_USER_IDX:
     s_user_paths[D_GCUSER_IDX] = s_user_paths[D_USER_IDX] + GC_USER_DIR DIR_SEP;
-    s_user_paths[D_WIIROOT_IDX] = s_user_paths[D_USER_IDX] + WII_USER_DIR;
+    s_user_paths[D_WIIROOT_IDX] = s_user_paths[D_USER_IDX] + WII_USER_DIR DIR_SEP;
     s_user_paths[D_CONFIG_IDX] = s_user_paths[D_USER_IDX] + CONFIG_DIR DIR_SEP;
     s_user_paths[D_GAMESETTINGS_IDX] = s_user_paths[D_USER_IDX] + GAMESETTINGS_DIR DIR_SEP;
     s_user_paths[D_MAPS_IDX] = s_user_paths[D_USER_IDX] + MAPS_DIR DIR_SEP;
@@ -978,7 +978,7 @@ static void RebuildUserDirectories(unsigned int dir_index)
     s_user_paths[F_ARAMDUMP_IDX] = s_user_paths[D_DUMP_IDX] + ARAM_DUMP;
     s_user_paths[F_FAKEVMEMDUMP_IDX] = s_user_paths[D_DUMP_IDX] + FAKEVMEM_DUMP;
     s_user_paths[F_GCSRAM_IDX] = s_user_paths[D_GCUSER_IDX] + GC_SRAM;
-    s_user_paths[F_WIISDCARD_IDX] = s_user_paths[D_WIIROOT_IDX] + DIR_SEP WII_SDCARD;
+    s_user_paths[F_WIISDCARD_IDX] = s_user_paths[D_WIIROOT_IDX] + WII_SDCARD;
 
     s_user_paths[D_MEMORYWATCHER_IDX] = s_user_paths[D_USER_IDX] + MEMORYWATCHER_DIR DIR_SEP;
     s_user_paths[F_MEMORYWATCHERLOCATIONS_IDX] =
diff --git a/Source/Core/Common/NandPaths.cpp b/Source/Core/Common/NandPaths.cpp
index 13dd1f2ce0..8fc33200d7 100644
--- a/Source/Core/Common/NandPaths.cpp
+++ b/Source/Core/Common/NandPaths.cpp
@@ -19,7 +19,9 @@ namespace Common
 std::string RootUserPath(FromWhichRoot from)
 {
   int idx = from == FROM_CONFIGURED_ROOT ? D_WIIROOT_IDX : D_SESSION_WIIROOT_IDX;
-  return File::GetUserPath(idx);
+  std::string dir = File::GetUserPath(idx);
+  dir.pop_back();  // remove trailing path separator
+  return dir;
 }
 
 static std::string RootUserPath(std::optional<FromWhichRoot> from)
diff --git a/Source/Core/Core/IOS/FS/HostBackend/FS.cpp b/Source/Core/Core/IOS/FS/HostBackend/FS.cpp
index b586dcee8f..2e2fee3f87 100644
--- a/Source/Core/Core/IOS/FS/HostBackend/FS.cpp
+++ b/Source/Core/Core/IOS/FS/HostBackend/FS.cpp
@@ -117,6 +117,8 @@ HostFileSystem::HostFileSystem(const std::string& root_path,
                                std::vector<NandRedirect> nand_redirects)
     : m_root_path{root_path}, m_nand_redirects(std::move(nand_redirects))
 {
+  while (StringEndsWith(m_root_path, "/"))
+    m_root_path.pop_back();
   File::CreateFullPath(m_root_path + "/");
   ResetFst();
   LoadFst();
diff --git a/Source/Core/Core/IOS/IOSC.cpp b/Source/Core/Core/IOS/IOSC.cpp
index 5f4461efbe..a937bad1ff 100644
--- a/Source/Core/Core/IOS/IOSC.cpp
+++ b/Source/Core/Core/IOS/IOSC.cpp
@@ -557,7 +557,7 @@ void IOSC::LoadDefaultEntries(ConsoleType console_type)
 
 void IOSC::LoadEntries()
 {
-  File::IOFile file{File::GetUserPath(D_WIIROOT_IDX) + "/keys.bin", "rb"};
+  File::IOFile file{File::GetUserPath(D_WIIROOT_IDX) + "keys.bin", "rb"};
   if (!file)
   {
     WARN_LOG_FMT(IOS, "keys.bin could not be found. Default values will be used.");
diff --git a/Source/Core/Core/WiiRoot.cpp b/Source/Core/Core/WiiRoot.cpp
index 149eb50627..de26bd4cf1 100644
--- a/Source/Core/Core/WiiRoot.cpp
+++ b/Source/Core/Core/WiiRoot.cpp
@@ -65,14 +65,14 @@ static bool CopyBackupFile(const std::string& path_from, const std::string& path
 
 static void DeleteBackupFile(const std::string& file_name)
 {
-  File::Delete(File::GetUserPath(D_BACKUP_IDX) + DIR_SEP + file_name);
+  File::Delete(File::GetUserPath(D_BACKUP_IDX) + file_name);
 }
 
 static void BackupFile(const std::string& path_in_nand)
 {
   const std::string file_name = PathToFileName(path_in_nand);
-  const std::string original_path = File::GetUserPath(D_WIIROOT_IDX) + DIR_SEP + path_in_nand;
-  const std::string backup_path = File::GetUserPath(D_BACKUP_IDX) + DIR_SEP + file_name;
+  const std::string original_path = File::GetUserPath(D_WIIROOT_IDX) + path_in_nand;
+  const std::string backup_path = File::GetUserPath(D_BACKUP_IDX) + file_name;
 
   CopyBackupFile(original_path, backup_path);
 }
@@ -80,8 +80,8 @@ static void BackupFile(const std::string& path_in_nand)
 static void RestoreFile(const std::string& path_in_nand)
 {
   const std::string file_name = PathToFileName(path_in_nand);
-  const std::string original_path = File::GetUserPath(D_WIIROOT_IDX) + DIR_SEP + path_in_nand;
-  const std::string backup_path = File::GetUserPath(D_BACKUP_IDX) + DIR_SEP + file_name;
+  const std::string original_path = File::GetUserPath(D_WIIROOT_IDX) + path_in_nand;
+  const std::string backup_path = File::GetUserPath(D_BACKUP_IDX) + file_name;
 
   if (CopyBackupFile(backup_path, original_path))
     DeleteBackupFile(file_name);
diff --git a/Source/Core/DiscIO/NANDImporter.cpp b/Source/Core/DiscIO/NANDImporter.cpp
index c836661813..ea72c3e6c4 100644
--- a/Source/Core/DiscIO/NANDImporter.cpp
+++ b/Source/Core/DiscIO/NANDImporter.cpp
@@ -34,10 +34,9 @@ void NANDImporter::ImportNANDBin(const std::string& path_to_bin,
   if (!ReadNANDBin(path_to_bin, get_otp_dump_path))
     return;
 
-  const std::string nand_root = File::GetUserPath(D_WIIROOT_IDX);
+  std::string nand_root = File::GetUserPath(D_WIIROOT_IDX);
+  nand_root.pop_back();  // remove trailing path separator
   m_nand_root_length = nand_root.length();
-  if (nand_root.back() == '/')
-    m_nand_root_length++;
 
   FindSuperblock();
   ProcessEntry(0, nand_root);