diff --git a/src/common/file_system.cpp b/src/common/file_system.cpp
index be3065487..2a09adfd5 100644
--- a/src/common/file_system.cpp
+++ b/src/common/file_system.cpp
@@ -1611,27 +1611,32 @@ bool FileSystem::EnsureDirectoryExists(const char* path, bool recursive, Error*
   return FileSystem::CreateDirectory(path, recursive, error);
 }
 
-bool FileSystem::RecursiveDeleteDirectory(const char* path)
+bool FileSystem::RecursiveDeleteDirectory(const char* path, Error* error)
 {
   FindResultsArray results;
   if (FindFiles(path, "*", FILESYSTEM_FIND_FILES | FILESYSTEM_FIND_FOLDERS | FILESYSTEM_FIND_HIDDEN_FILES, &results))
   {
     for (const FILESYSTEM_FIND_DATA& fd : results)
     {
-      if (fd.Attributes & FILESYSTEM_FILE_ATTRIBUTE_DIRECTORY)
+      // don't recurse into symlinked directories, just remove the link itself
+      if ((fd.Attributes & (FILESYSTEM_FILE_ATTRIBUTE_DIRECTORY | FILESYSTEM_FILE_ATTRIBUTE_LINK)) ==
+          FILESYSTEM_FILE_ATTRIBUTE_DIRECTORY)
       {
-        if (!RecursiveDeleteDirectory(fd.FileName.c_str()))
+        if (!RecursiveDeleteDirectory(fd.FileName.c_str(), error))
           return false;
       }
       else
       {
-        if (!DeleteFile(fd.FileName.c_str()))
+        if (!DeleteFile(fd.FileName.c_str(), error))
+        {
+          Error::AddPrefixFmt(error, "Failed to delete {}: ", fd.FileName);
           return false;
+        }
       }
     }
   }
 
-  return DeleteDirectory(path);
+  return DeleteDirectory(path, error);
 }
 
 bool FileSystem::CopyFilePath(const char* source, const char* destination, bool replace)
@@ -2156,17 +2161,32 @@ bool FileSystem::CreateDirectory(const char* Path, bool Recursive, Error* error)
 bool FileSystem::DeleteFile(const char* path, Error* error)
 {
   const std::wstring wpath = GetWin32Path(path);
+
+  // Need to handle both links/junctions and files as per unix.
   const DWORD fileAttributes = GetFileAttributesW(wpath.c_str());
-  if (fileAttributes == INVALID_FILE_ATTRIBUTES || fileAttributes & FILE_ATTRIBUTE_DIRECTORY)
+  if (fileAttributes == INVALID_FILE_ATTRIBUTES ||
+      ((fileAttributes & (FILE_ATTRIBUTE_DIRECTORY | FILE_ATTRIBUTE_REPARSE_POINT)) == FILE_ATTRIBUTE_DIRECTORY))
   {
     Error::SetStringView(error, "File does not exist.");
     return false;
   }
 
-  if (!DeleteFileW(wpath.c_str()))
+  // if it's a junction/symlink, we need to use RemoveDirectory() instead
+  if (fileAttributes & FILE_ATTRIBUTE_DIRECTORY)
   {
-    Error::SetWin32(error, "DeleteFileW() failed: ", GetLastError());
-    return false;
+    if (!RemoveDirectoryW(wpath.c_str()))
+    {
+      Error::SetWin32(error, "RemoveDirectoryW() failed: ", GetLastError());
+      return false;
+    }
+  }
+  else
+  {
+    if (!DeleteFileW(wpath.c_str()))
+    {
+      Error::SetWin32(error, "DeleteFileW() failed: ", GetLastError());
+      return false;
+    }
   }
 
   return true;
@@ -2186,10 +2206,23 @@ bool FileSystem::RenamePath(const char* old_path, const char* new_path, Error* e
   return true;
 }
 
-bool FileSystem::DeleteDirectory(const char* path)
+bool FileSystem::DeleteDirectory(const char* path, Error* error)
 {
   const std::wstring wpath = GetWin32Path(path);
-  return RemoveDirectoryW(wpath.c_str());
+  const DWORD fileAttributes = GetFileAttributesW(wpath.c_str());
+  if (fileAttributes == INVALID_FILE_ATTRIBUTES || !(fileAttributes & FILE_ATTRIBUTE_DIRECTORY))
+  {
+    Error::SetStringView(error, "File does not exist.");
+    return false;
+  }
+
+  if (!RemoveDirectoryW(wpath.c_str()))
+  {
+    Error::SetWin32(error, "RemoveDirectoryW() failed: ", GetLastError());
+    return false;
+  }
+
+  return true;
 }
 
 std::string FileSystem::GetProgramPath()
@@ -2273,10 +2306,10 @@ bool FileSystem::SetPathCompression(const char* path, bool enable)
 
 #elif !defined(__ANDROID__)
 
-static u32 TranslateStatAttributes(struct stat& st)
+static u32 TranslateStatAttributes(struct stat& st, struct stat& st_link)
 {
   return (S_ISDIR(st.st_mode) ? FILESYSTEM_FILE_ATTRIBUTE_DIRECTORY : 0) |
-         (S_ISLNK(st.st_mode) ? FILESYSTEM_FILE_ATTRIBUTE_LINK : 0);
+         (S_ISLNK(st_link.st_mode) ? FILESYSTEM_FILE_ATTRIBUTE_LINK : 0);
 }
 
 static u32 RecursiveFindFiles(const char* OriginPath, const char* ParentPath, const char* Path, const char* Pattern,
@@ -2330,12 +2363,12 @@ static u32 RecursiveFindFiles(const char* OriginPath, const char* ParentPath, co
     else
       full_path = fmt::format("{}/{}", OriginPath, pDirEnt->d_name);
 
-    struct stat sDir;
-    if (stat(full_path.c_str(), &sDir) < 0)
+    struct stat sDir, sDirLink;
+    if (stat(full_path.c_str(), &sDir) < 0 || lstat(full_path.c_str(), &sDirLink) < 0)
       continue;
 
     FILESYSTEM_FIND_DATA outData;
-    outData.Attributes = TranslateStatAttributes(sDir);
+    outData.Attributes = TranslateStatAttributes(sDir, sDirLink);
 
     if (S_ISDIR(sDir.st_mode))
     {
@@ -2478,18 +2511,18 @@ bool FileSystem::StatFile(std::FILE* fp, struct stat* st, Error* error)
 bool FileSystem::StatFile(const char* path, FILESYSTEM_STAT_DATA* sd, Error* error)
 {
   // stat file
-  struct stat sysStatData;
-  if (stat(path, &sysStatData) < 0)
+  struct stat ssd, ssd_link;
+  if (stat(path, &ssd) < 0 || lstat(path, &ssd_link) < 0)
   {
     Error::SetErrno(error, "stat() failed: ", errno);
     return false;
   }
 
   // parse attributes
-  sd->CreationTime = sysStatData.st_ctime;
-  sd->ModificationTime = sysStatData.st_mtime;
-  sd->Attributes = TranslateStatAttributes(sysStatData);
-  sd->Size = S_ISREG(sysStatData.st_mode) ? sysStatData.st_size : 0;
+  sd->CreationTime = ssd.st_ctime;
+  sd->ModificationTime = ssd.st_mtime;
+  sd->Attributes = TranslateStatAttributes(ssd, ssd_link);
+  sd->Size = S_ISREG(ssd.st_mode) ? ssd.st_size : 0;
 
   // ok
   return true;
@@ -2505,18 +2538,18 @@ bool FileSystem::StatFile(std::FILE* fp, FILESYSTEM_STAT_DATA* sd, Error* error)
   }
 
   // stat file
-  struct stat sysStatData;
-  if (fstat(fd, &sysStatData) != 0)
+  struct stat ssd;
+  if (fstat(fd, &ssd) != 0)
   {
     Error::SetErrno(error, "stat() failed: ", errno);
     return false;
   }
 
   // parse attributes
-  sd->CreationTime = sysStatData.st_ctime;
-  sd->ModificationTime = sysStatData.st_mtime;
-  sd->Attributes = TranslateStatAttributes(sysStatData);
-  sd->Size = S_ISREG(sysStatData.st_mode) ? sysStatData.st_size : 0;
+  sd->CreationTime = ssd.st_ctime;
+  sd->ModificationTime = ssd.st_mtime;
+  sd->Attributes = TranslateStatAttributes(ssd, ssd);
+  sd->Size = S_ISREG(ssd.st_mode) ? ssd.st_size : 0;
 
   return true;
 }
@@ -2655,8 +2688,8 @@ bool FileSystem::CreateDirectory(const char* path, bool recursive, Error* error)
 
 bool FileSystem::DeleteFile(const char* path, Error* error)
 {
-  struct stat sysStatData;
-  if (stat(path, &sysStatData) != 0 || S_ISDIR(sysStatData.st_mode))
+  struct stat sd;
+  if (lstat(path, &sd) != 0 || (S_ISDIR(sd.st_mode) && !S_ISLNK(sd.st_mode)))
   {
     Error::SetStringView(error, "File does not exist.");
     return false;
@@ -2675,21 +2708,38 @@ bool FileSystem::RenamePath(const char* old_path, const char* new_path, Error* e
 {
   if (rename(old_path, new_path) != 0)
   {
-    const int err = errno;
-    Error::SetErrno(error, "rename() failed: ", err);
+    Error::SetErrno(error, "rename() failed: ", errno);
     return false;
   }
 
   return true;
 }
 
-bool FileSystem::DeleteDirectory(const char* path)
+bool FileSystem::DeleteDirectory(const char* path, Error* error)
 {
-  struct stat sysStatData;
-  if (stat(path, &sysStatData) != 0 || !S_ISDIR(sysStatData.st_mode))
+  struct stat sd;
+  if (stat(path, &sd) != 0 || !S_ISDIR(sd.st_mode))
     return false;
 
-  return (rmdir(path) == 0);
+  // if it's a symlink, use unlink() instead
+  if (S_ISLNK(sd.st_mode))
+  {
+    if (unlink(path) != 0)
+    {
+      Error::SetErrno(error, "unlink() failed: ", errno);
+      return false;
+    }
+  }
+  else
+  {
+    if (rmdir(path) != 0)
+    {
+      Error::SetErrno(error, "rmdir() failed: ", errno);
+      return false;
+    }
+  }
+
+  return true;
 }
 
 std::string FileSystem::GetProgramPath()
diff --git a/src/common/file_system.h b/src/common/file_system.h
index 654fa28e2..155e94187 100644
--- a/src/common/file_system.h
+++ b/src/common/file_system.h
@@ -202,10 +202,10 @@ bool CreateDirectory(const char* path, bool recursive, Error* error = nullptr);
 bool EnsureDirectoryExists(const char* path, bool recursive, Error* error = nullptr);
 
 /// Removes a directory.
-bool DeleteDirectory(const char* path);
+bool DeleteDirectory(const char* path, Error* error = nullptr);
 
 /// Recursively removes a directory and all subdirectories/files.
-bool RecursiveDeleteDirectory(const char* path);
+bool RecursiveDeleteDirectory(const char* path, Error* error = nullptr);
 
 /// Copies one file to another, optionally replacing it if it already exists.
 bool CopyFilePath(const char* source, const char* destination, bool replace);
diff --git a/src/updater/updater.cpp b/src/updater/updater.cpp
index e2350fe50..14b5105f7 100644
--- a/src/updater/updater.cpp
+++ b/src/updater/updater.cpp
@@ -133,22 +133,27 @@ bool Updater::RecursiveDeleteDirectory(const char* path, bool remove_dir)
 
   return true;
 #else
+  Error error;
   FileSystem::FindResultsArray results;
   if (FileSystem::FindFiles(path, "*", FILESYSTEM_FIND_FILES | FILESYSTEM_FIND_FOLDERS | FILESYSTEM_FIND_HIDDEN_FILES,
                             &results))
   {
     for (const FILESYSTEM_FIND_DATA& fd : results)
     {
-      if (fd.Attributes & FILESYSTEM_FILE_ATTRIBUTE_DIRECTORY)
+      if ((fd.Attributes & (FILESYSTEM_FILE_ATTRIBUTE_DIRECTORY | FILESYSTEM_FILE_ATTRIBUTE_LINK)) ==
+          FILESYSTEM_FILE_ATTRIBUTE_DIRECTORY)
       {
         if (!RecursiveDeleteDirectory(fd.FileName.c_str(), true))
           return false;
       }
       else
       {
-        m_progress->FormatInformation("Removing directory '{}'.", fd.FileName);
-        if (!FileSystem::DeleteFile(fd.FileName.c_str()))
+        m_progress->FormatInformation("Removing file '{}'.", fd.FileName);
+        if (!FileSystem::DeleteFile(fd.FileName.c_str(), &error))
+        {
+          m_progress->FormatModalError("DeleteFile({}) failed: {}", fd.FileName, error.GetDescription());
           return false;
+        }
       }
     }
   }
@@ -157,7 +162,13 @@ bool Updater::RecursiveDeleteDirectory(const char* path, bool remove_dir)
     return true;
 
   m_progress->FormatInformation("Removing directory '{}'.", path);
-  return FileSystem::DeleteDirectory(path);
+  if (!FileSystem::DeleteDirectory(path, &error))
+  {
+    m_progress->FormatModalError("DeleteDirectory({}) failed: {}", path, error.GetDescription());
+    return false;
+  }
+
+  return true;
 #endif
 }