diff --git a/source/blender/editors/include/ED_fileselect.hh b/source/blender/editors/include/ED_fileselect.hh
index a2c3351e58a..4cceb1f6c19 100644
--- a/source/blender/editors/include/ED_fileselect.hh
+++ b/source/blender/editors/include/ED_fileselect.hh
@@ -8,6 +8,10 @@
 
 #pragma once
 
+#include <string>
+
+#include "BLI_vector.hh"
+
 #include "DNA_uuid_types.h"
 
 struct ARegion;
@@ -203,6 +207,8 @@ ScrArea *ED_fileselect_handler_area_find_any_with_op(const wmWindow *win);
  */
 void ED_fileselect_ensure_default_filepath(bContext *C, wmOperator *op, const char *extension);
 
+blender::Vector<std::string> ED_fileselect_selected_files_full_paths(const SpaceFile *sfile);
+
 /* TODO: Maybe we should move this to BLI?
  * On the other hand, it's using defines from space-file area, so not sure... */
 int ED_path_extension_type(const char *path);
diff --git a/source/blender/editors/io/io_drop_import_file.cc b/source/blender/editors/io/io_drop_import_file.cc
index 093b0488531..a7fb0174472 100644
--- a/source/blender/editors/io/io_drop_import_file.cc
+++ b/source/blender/editors/io/io_drop_import_file.cc
@@ -3,6 +3,7 @@
  * SPDX-License-Identifier: GPL-2.0-or-later */
 
 #include "BLI_path_utils.hh"
+#include "BLI_string.h"
 
 #include "BLT_translation.hh"
 
@@ -60,9 +61,9 @@ static void file_handler_import_operator_write_ptr(
   }
 
   PropertyRNA *directory_prop = RNA_struct_find_property_check(props, "directory", PROP_STRING);
+  char dir[FILE_MAX];
+  BLI_path_split_dir_part(paths[0].c_str(), dir, sizeof(dir));
   if (directory_prop) {
-    char dir[FILE_MAX];
-    BLI_path_split_dir_part(paths[0].c_str(), dir, sizeof(dir));
     RNA_property_string_set(&props, directory_prop, dir);
   }
 
@@ -72,7 +73,8 @@ static void file_handler_import_operator_write_ptr(
     RNA_property_collection_clear(&props, files_prop);
     for (const auto &index : supported_paths) {
       char file[FILE_MAX];
-      BLI_path_split_file_part(paths[index].c_str(), file, sizeof(file));
+      STRNCPY(file, paths[index].c_str());
+      BLI_path_rel(file, dir);
 
       PointerRNA item_ptr{};
       RNA_property_collection_add(&props, files_prop, &item_ptr);
diff --git a/source/blender/editors/io/io_utils.cc b/source/blender/editors/io/io_utils.cc
index 47b7d8eab04..a18af9e90bb 100644
--- a/source/blender/editors/io/io_utils.cc
+++ b/source/blender/editors/io/io_utils.cc
@@ -5,6 +5,7 @@
 #include <fmt/format.h>
 
 #include "BLI_path_utils.hh"
+#include "BLI_string.h"
 
 #include "BLT_translation.hh"
 
@@ -96,6 +97,7 @@ Vector<std::string> paths_from_operator_properties(PointerRNA *ptr)
       RNA_string_get(&file_ptr, "name", name);
       char path[FILE_MAX];
       BLI_path_join(path, sizeof(path), directory, name);
+      BLI_path_normalize(path);
       paths.append_non_duplicates(path);
     }
     RNA_PROP_END;
@@ -121,7 +123,8 @@ void paths_to_operator_properties(PointerRNA *ptr, const Span<std::string> paths
   RNA_collection_clear(ptr, "files");
   for (const auto &path : paths) {
     char file[FILE_MAX];
-    BLI_path_split_file_part(path.c_str(), file, sizeof(file));
+    STRNCPY(file, path.c_str());
+    BLI_path_rel(file, dir);
 
     PointerRNA itemptr{};
     RNA_collection_add(ptr, "files", &itemptr);
diff --git a/source/blender/editors/space_file/filesel.cc b/source/blender/editors/space_file/filesel.cc
index 75c626d1081..390c0f2cc99 100644
--- a/source/blender/editors/space_file/filesel.cc
+++ b/source/blender/editors/space_file/filesel.cc
@@ -1502,3 +1502,17 @@ void ED_fileselect_ensure_default_filepath(bContext *C, wmOperator *op, const ch
     RNA_string_set(op->ptr, "filepath", filepath);
   }
 }
+
+blender::Vector<std::string> ED_fileselect_selected_files_full_paths(const SpaceFile *sfile)
+{
+  blender::Vector<std::string> paths;
+  char path[FILE_MAX_LIBEXTRA];
+  for (const int i : blender::IndexRange(filelist_files_ensure(sfile->files))) {
+    if (filelist_entry_is_selected(sfile->files, i)) {
+      const FileDirEntry *entry = filelist_file(sfile->files, i);
+      filelist_file_get_full_path(sfile->files, entry, path);
+      paths.append(path);
+    }
+  }
+  return paths;
+}
diff --git a/source/blender/windowmanager/intern/wm_dragdrop.cc b/source/blender/windowmanager/intern/wm_dragdrop.cc
index 5164d91c677..0d7ed152b84 100644
--- a/source/blender/windowmanager/intern/wm_dragdrop.cc
+++ b/source/blender/windowmanager/intern/wm_dragdrop.cc
@@ -21,7 +21,6 @@
 
 #include "BLT_translation.hh"
 
-#include "BLI_linear_allocator.hh"
 #include "BLI_listbase.h"
 #include "BLI_math_color.h"
 #include "BLI_path_utils.hh"
@@ -365,21 +364,15 @@ void WM_event_drag_image(wmDrag *drag, const ImBuf *imb, float scale)
 void WM_event_drag_path_override_poin_data_with_space_file_paths(const bContext *C, wmDrag *drag)
 {
   BLI_assert(drag->type == WM_DRAG_PATH);
-  if (!CTX_wm_space_file(C)) {
+  const SpaceFile *sfile = CTX_wm_space_file(C);
+  if (!sfile) {
     return;
   }
-  char dirpath[FILE_MAX];
-  BLI_path_split_dir_part(WM_drag_get_single_path(drag), dirpath, FILE_MAX);
-
-  blender::LinearAllocator<> allocator;
+  const blender::Vector<std::string> selected_paths = ED_fileselect_selected_files_full_paths(
+      sfile);
   blender::Vector<const char *> paths;
-  const blender::Vector<PointerRNA> files = CTX_data_collection_get(C, "selected_files");
-  for (const PointerRNA &file_ptr : files) {
-    const FileDirEntry *file = static_cast<const FileDirEntry *>(file_ptr.data);
-    char filepath[FILE_MAX];
-    BLI_path_join(filepath, sizeof(filepath), dirpath, file->name);
-
-    paths.append(allocator.copy_string(filepath).c_str());
+  for (const std::string &path : selected_paths) {
+    paths.append(path.c_str());
   }
   if (paths.is_empty()) {
     return;