diff --git a/kernel/src/Api/BuildNo.hpp b/kernel/src/Api/BuildNo.hpp
index 34ee96d..3ca90c7 100644
--- a/kernel/src/Api/BuildNo.hpp
+++ b/kernel/src/Api/BuildNo.hpp
@@ -12,4 +12,4 @@
 
 #pragma once
 
-#define MONTAUK_BUILD_NUMBER 4
+#define MONTAUK_BUILD_NUMBER 5
diff --git a/programs/include/gui/desktop.hpp b/programs/include/gui/desktop.hpp
index 8f76ee5..59c7168 100644
--- a/programs/include/gui/desktop.hpp
+++ b/programs/include/gui/desktop.hpp
@@ -46,6 +46,9 @@ struct DesktopItem {
     bool menu_visible;
     bool launch_with_home;
     bool admin_only;
+    // File extensions the app opens (manifest files.types): lowercase, no dot,
+    // space-separated with a leading and trailing space, e.g. " jpg jpeg ".
+    char file_types[160];
 };
 
 enum LauncherItemKind : uint8_t {
@@ -121,6 +124,10 @@ struct DesktopState {
     int launcher_scroll;
     bool super_left_down;
     bool super_right_down;
+    // Live modifier state, tracked from every key event (modifier presses and
+    // releases are delivered too) so mouse handlers can see Ctrl/Shift.
+    bool kbd_shift_down;
+    bool kbd_ctrl_down;
 
     SvgIcon icon_terminal;
     SvgIcon icon_filemanager;
diff --git a/programs/src/desktop/apps/filemanager/actions.cpp b/programs/src/desktop/apps/filemanager/actions.cpp
index 0b91715..29b0d6a 100644
--- a/programs/src/desktop/apps/filemanager/actions.cpp
+++ b/programs/src/desktop/apps/filemanager/actions.cpp
@@ -49,6 +49,9 @@ void filemanager_do_paste(FileManagerState* fm) {
 
 void filemanager_start_rename(FileManagerState* fm) {
     if (fm->selected < 0 || fm->selected >= fm->entry_count) return;
+    // Rename is single-target; with several entries selected, `selected` is
+    // only the focus and renaming it would be a surprise.
+    if (fm->multi_count > 1) return;
     if (filemanager_is_computer_view(fm) || filemanager_is_virtual_view(fm) ||
         fm->entry_types[fm->selected] == FM_ENTRY_DRIVE) return;
 
@@ -228,10 +231,14 @@ void filemanager_open_ctx_menu(FileManagerState* fm, int local_x, int local_y, i
             fm->ctx_items[fm->ctx_item_count++] = CTX_OPEN;
             fm->ctx_items[fm->ctx_item_count++] = CTX_PROPERTIES;
         } else {
+            bool several = fm->multi_count > 1;
             fm->ctx_items[fm->ctx_item_count++] = CTX_OPEN;
+            if (!several && !fm->is_dir[target_idx])
+                fm->ctx_items[fm->ctx_item_count++] = CTX_OPEN_WITH;
             fm->ctx_items[fm->ctx_item_count++] = CTX_COPY;
             fm->ctx_items[fm->ctx_item_count++] = CTX_CUT;
-            fm->ctx_items[fm->ctx_item_count++] = CTX_RENAME;
+            if (!several)
+                fm->ctx_items[fm->ctx_item_count++] = CTX_RENAME;
             fm->ctx_items[fm->ctx_item_count++] = CTX_DELETE;
             fm->ctx_items[fm->ctx_item_count++] = CTX_PROPERTIES;
         }
@@ -247,6 +254,13 @@ void filemanager_open_ctx_menu(FileManagerState* fm, int local_x, int local_y, i
             if (fm->clipboard_count > 0)
                 fm->ctx_items[fm->ctx_item_count++] = CTX_PASTE;
             fm->ctx_items[fm->ctx_item_count++] = CTX_NEW_FOLDER;
+            if (fm->entry_count > 0)
+                fm->ctx_items[fm->ctx_item_count++] = CTX_SELECT_ALL;
+            fm->ctx_items[fm->ctx_item_count++] = CTX_SORT_NAME;
+            fm->ctx_items[fm->ctx_item_count++] = CTX_SORT_SIZE;
+            fm->ctx_items[fm->ctx_item_count++] = CTX_SORT_TYPE;
+            fm->ctx_items[fm->ctx_item_count++] = CTX_SORT_MODIFIED;
+            fm->ctx_items[fm->ctx_item_count++] = CTX_REFRESH;
         }
     }
 }
diff --git a/programs/src/desktop/apps/filemanager/app.cpp b/programs/src/desktop/apps/filemanager/app.cpp
index 6ffab89..11f630c 100644
--- a/programs/src/desktop/apps/filemanager/app.cpp
+++ b/programs/src/desktop/apps/filemanager/app.cpp
@@ -37,6 +37,7 @@ static void open_filemanager_internal(DesktopState* ds, const char* initial_path
     FileManagerState* fm = (FileManagerState*)montauk::malloc(sizeof(FileManagerState));
     montauk::memset(fm, 0, sizeof(FileManagerState));
     fm->selected = -1;
+    fm->sel_anchor = -1;
     fm->last_click_item = -1;
     fm->history_pos = -1;
     fm->history_count = 0;
diff --git a/programs/src/desktop/apps/filemanager/events.cpp b/programs/src/desktop/apps/filemanager/events.cpp
index f5f31c7..36339a4 100644
--- a/programs/src/desktop/apps/filemanager/events.cpp
+++ b/programs/src/desktop/apps/filemanager/events.cpp
@@ -8,6 +8,51 @@
 
 namespace filemanager {
 
+static void filemanager_show_selection_properties(FileManagerState* fm, int target) {
+    if (fm->multi_count > 1 && fm->entry_count > 0) {
+        int* sel = (int*)montauk::malloc((uint64_t)fm->entry_count * sizeof(int));
+        if (sel) {
+            int n = filemanager_collect_selection(fm, sel, fm->entry_count);
+            if (n > 0) filemanager_show_multi_properties(fm, sel, n);
+            montauk::mfree(sel);
+        }
+    } else {
+        filemanager_show_properties(fm, target);
+    }
+}
+
+static bool filemanager_is_listing(const FileManagerState* fm) {
+    return !filemanager_is_computer_view(fm) && !filemanager_is_virtual_view(fm);
+}
+
+// Left click on an entry. Ctrl toggles it, Shift selects the range from the
+// anchor (Ctrl+Shift adds that range); a plain click selects it alone, and a
+// second plain click within 400 ms opens it.
+static void filemanager_click_entry(FileManagerState* fm, int idx) {
+    DesktopState* ds = fm->desktop;
+    bool ctrl = ds && ds->kbd_ctrl_down;
+    bool shift = ds && ds->kbd_shift_down;
+
+    if (ctrl || shift) {
+        if (shift) filemanager_select_range(fm, idx, ctrl);
+        else filemanager_toggle_selection(fm, idx);
+        fm->last_click_item = -1;
+        fm->last_click_time = 0;
+        return;
+    }
+
+    uint64_t now = montauk::get_milliseconds();
+    if (fm->last_click_item == idx && (now - fm->last_click_time) < 400) {
+        filemanager_open_entry(fm, idx);
+        fm->last_click_item = -1;
+        fm->last_click_time = 0;
+    } else {
+        filemanager_select_single(fm, idx);
+        fm->last_click_item = idx;
+        fm->last_click_time = now;
+    }
+}
+
 void filemanager_on_mouse(Window* win, MouseEvent& ev) {
     FileManagerState* fm = (FileManagerState*)win->app_data;
     if (!fm) return;
@@ -26,13 +71,14 @@ void filemanager_on_mouse(Window* win, MouseEvent& ev) {
     // ---- Context menu interaction ----
     if (fm->ctx_open) {
         mtk::ContextMenuState state = filemanager_context_state(fm);
-        mtk::ContextMenuItem items[8];
-        filemanager_build_context_items(fm, items, 8);
+        mtk::ContextMenuItem items[FM_CTX_MAX_ITEMS];
+        filemanager_build_context_items(fm, items, FM_CTX_MAX_ITEMS);
         int action = mtk::context_menu_handle_mouse(state, items,
                                                     fm->ctx_item_count,
                                                     local_x, local_y,
                                                     ev.buttons, ev.prev_buttons,
-                                                    cw, win->content_h);
+                                                    cw, win->content_h,
+                                                    FM_CTX_MENU_W);
         filemanager_store_context_state(fm, state);
 
         if (action >= 0) {
@@ -50,20 +96,14 @@ void filemanager_on_mouse(Window* win, MouseEvent& ev) {
             case CTX_RENAME:     filemanager_start_rename(fm); break;
             case CTX_DELETE:     filemanager_delete_selected(fm); break;
             case CTX_NEW_FOLDER: filemanager_new_folder(fm); break;
-            case CTX_PROPERTIES: {
-                if (fm->multi_count > 1 && fm->entry_count > 0) {
-                    int* sel = (int*)montauk::malloc((uint64_t)fm->entry_count * sizeof(int));
-                    if (sel) {
-                        int n = filemanager_collect_selection(fm, sel, fm->entry_count);
-                        if (n > 0) filemanager_show_multi_properties(fm, sel, n);
-                        montauk::mfree(sel);
-                    }
-                } else {
-                    filemanager_show_properties(fm, target);
-                }
-                break;
-            }
+            case CTX_PROPERTIES: filemanager_show_selection_properties(fm, target); break;
             case CTX_REFRESH:    filemanager_refresh(fm); break;
+            case CTX_OPEN_WITH:  filemanager_show_open_with(fm, target); break;
+            case CTX_SELECT_ALL: filemanager_select_all(fm); break;
+            case CTX_SORT_NAME:  filemanager_set_sort(fm, FM_SORT_NAME); break;
+            case CTX_SORT_SIZE:  filemanager_set_sort(fm, FM_SORT_SIZE); break;
+            case CTX_SORT_TYPE:  filemanager_set_sort(fm, FM_SORT_TYPE); break;
+            case CTX_SORT_MODIFIED: filemanager_set_sort(fm, FM_SORT_MODIFIED); break;
             }
             return;
         }
@@ -123,23 +163,10 @@ void filemanager_on_mouse(Window* win, MouseEvent& ev) {
                 int clicked_idx = filemanager_grid_index_at(fm, cols, local_x, rel_y);
 
                 if (clicked_idx >= 0 && clicked_idx < fm->entry_count) {
-                    uint64_t now = montauk::get_milliseconds();
-                    filemanager_clear_multi_selection(fm);
-
-                    if (fm->last_click_item == clicked_idx &&
-                        (now - fm->last_click_time) < 400) {
-                        filemanager_open_entry(fm, clicked_idx);
-                        fm->last_click_item = -1;
-                        fm->last_click_time = 0;
-                    } else {
-                        fm->selected = clicked_idx;
-                        fm->last_click_item = clicked_idx;
-                        fm->last_click_time = now;
-                    }
+                    filemanager_click_entry(fm, clicked_idx);
                 } else {
                     // Background click in grid area: start marquee drag
-                    fm->selected = -1;
-                    filemanager_clear_multi_selection(fm);
+                    filemanager_select_single(fm, -1);
                     fm->marquee_active = true;
                     fm->marquee_start_x = local_x;
                     fm->marquee_start_y = rel_y;
@@ -149,30 +176,30 @@ void filemanager_on_mouse(Window* win, MouseEvent& ev) {
             }
         } else {
             // List view clicks
-            int list_y = FM_TOOLBAR_H + FM_PATHBAR_H + FM_HEADER_H;
+            int header_y = FM_TOOLBAR_H + FM_PATHBAR_H;
+            int list_y = header_y + FM_HEADER_H;
+            if (local_y >= header_y && local_y < list_y && filemanager_is_listing(fm)) {
+                // Column header click: sort by that column (again = reverse).
+                FileManagerListColumns cols = filemanager_list_columns(cw);
+                if (cols.type_x >= 0 && local_x >= cols.type_x)
+                    filemanager_set_sort(fm, FM_SORT_TYPE);
+                else if (cols.size_x >= 0 && local_x >= cols.size_x)
+                    filemanager_set_sort(fm, FM_SORT_SIZE);
+                else if (cols.modified_x >= 0 && local_x >= cols.modified_x - 4)
+                    filemanager_set_sort(fm, FM_SORT_MODIFIED);
+                else
+                    filemanager_set_sort(fm, FM_SORT_NAME);
+                return;
+            }
             if (local_y >= list_y && local_x < cw - FM_SCROLLBAR_W) {
                 int rel_y = local_y - list_y + fm->scrollbar.scroll_offset;
                 int clicked_idx = rel_y / FM_ITEM_H;
 
                 if (clicked_idx >= 0 && clicked_idx < fm->entry_count) {
-                    uint64_t now = montauk::get_milliseconds();
-                    filemanager_clear_multi_selection(fm);
-
-                    // Double-click detection
-                    if (fm->last_click_item == clicked_idx &&
-                        (now - fm->last_click_time) < 400) {
-                        filemanager_open_entry(fm, clicked_idx);
-                        fm->last_click_item = -1;
-                        fm->last_click_time = 0;
-                    } else {
-                        fm->selected = clicked_idx;
-                        fm->last_click_item = clicked_idx;
-                        fm->last_click_time = now;
-                    }
+                    filemanager_click_entry(fm, clicked_idx);
                 } else {
                     // Background click in list area: start marquee drag
-                    fm->selected = -1;
-                    filemanager_clear_multi_selection(fm);
+                    filemanager_select_single(fm, -1);
                     fm->marquee_active = true;
                     fm->marquee_start_x = local_x;
                     fm->marquee_start_y = rel_y;
@@ -271,13 +298,10 @@ void filemanager_on_mouse(Window* win, MouseEvent& ev) {
                         target_idx = idx;
                         // Preserve multi-selection if right-clicking inside it,
                         // otherwise replace it with a single selection.
-                        if (!(fm->multi_count > 0 && fm->multi_selected[idx])) {
-                            filemanager_clear_multi_selection(fm);
-                            fm->selected = idx;
-                        }
+                        if (!filemanager_is_entry_selected(fm, idx))
+                            filemanager_select_single(fm, idx);
                     } else {
-                        filemanager_clear_multi_selection(fm);
-                        fm->selected = -1;
+                        filemanager_select_single(fm, -1);
                     }
                 }
             } else {
@@ -289,13 +313,10 @@ void filemanager_on_mouse(Window* win, MouseEvent& ev) {
                         target_idx = idx;
                         // Preserve multi-selection if right-clicking inside it,
                         // otherwise replace it with a single selection.
-                        if (!(fm->multi_count > 0 && fm->multi_selected[idx])) {
-                            filemanager_clear_multi_selection(fm);
-                            fm->selected = idx;
-                        }
+                        if (!filemanager_is_entry_selected(fm, idx))
+                            filemanager_select_single(fm, idx);
                     } else {
-                        filemanager_clear_multi_selection(fm);
-                        fm->selected = -1;
+                        filemanager_select_single(fm, -1);
                     }
                 }
             }
@@ -319,27 +340,103 @@ void filemanager_on_mouse(Window* win, MouseEvent& ev) {
     }
 }
 
-// Keep the selected row inside the visible list area so arrow-key navigation
+static int filemanager_grid_cols(Window* win) {
+    int cols = (win->content_rect().w - FM_SCROLLBAR_W) / FM_GRID_CELL_W;
+    return cols < 1 ? 1 : cols;
+}
+
+// Keep the focused entry inside the visible area so keyboard navigation
 // scrolls the view along with the selection.
 static void filemanager_scroll_to_selected(Window* win, FileManagerState* fm) {
-    if (fm->grid_view) return;
     if (fm->selected < 0 || fm->selected >= fm->entry_count) return;
 
-    int list_y = FM_TOOLBAR_H + FM_PATHBAR_H + FM_HEADER_H;
+    int list_y = fm->grid_view ? FM_TOOLBAR_H + FM_PATHBAR_H
+                               : FM_TOOLBAR_H + FM_PATHBAR_H + FM_HEADER_H;
     int list_h = win->content_h - list_y;
     if (list_h <= 0) return;
 
-    int top = fm->selected * FM_ITEM_H;
+    int top, item_h, content_h;
+    if (fm->grid_view) {
+        int cols = filemanager_grid_cols(win);
+        int row = fm->selected / cols;
+        top = filemanager_grid_row_y(fm, row, cols);
+        item_h = filemanager_grid_row_height(fm, row, cols);
+        content_h = filemanager_grid_content_height(fm, cols);
+    } else {
+        top = fm->selected * FM_ITEM_H;
+        item_h = FM_ITEM_H;
+        content_h = fm->entry_count * FM_ITEM_H;
+    }
+
     int off = fm->scrollbar.scroll_offset;
     if (top < off) off = top;
-    else if (top + FM_ITEM_H > off + list_h) off = top + FM_ITEM_H - list_h;
+    else if (top + item_h > off + list_h) off = top + item_h - list_h;
 
-    int max_scroll = fm->entry_count * FM_ITEM_H - list_h;
+    int max_scroll = content_h - list_h;
     if (off > max_scroll) off = max_scroll;
     if (off < 0) off = 0;
     fm->scrollbar.scroll_offset = off;
 }
 
+// Move keyboard focus to target (clamped). With extend (Shift held) the
+// selection grows from the anchor instead of moving with the focus.
+static void filemanager_move_focus(Window* win, FileManagerState* fm, int target, bool extend) {
+    if (fm->entry_count <= 0) return;
+    if (target < 0) target = 0;
+    if (target >= fm->entry_count) target = fm->entry_count - 1;
+    if (extend) filemanager_select_range(fm, target, false);
+    else filemanager_select_single(fm, target);
+    filemanager_scroll_to_selected(win, fm);
+}
+
+static bool filemanager_prefix_match_ci(const char* name, const char* prefix, int len) {
+    for (int i = 0; i < len; i++) {
+        char a = name[i];
+        char b = prefix[i];
+        if (!a) return false;
+        if (a >= 'A' && a <= 'Z') a += 32;
+        if (b >= 'A' && b <= 'Z') b += 32;
+        if (a != b) return false;
+    }
+    return true;
+}
+
+// Type-to-jump. Keys typed within a second of each other build up a prefix;
+// repeating a single character instead cycles through the names starting
+// with it.
+static void filemanager_typeahead(Window* win, FileManagerState* fm,
+                                  const montauk::abi::KeyEvent& key) {
+    char ch[4];
+    int n = montauk::utf8::key_utf8(key, ch);
+    if (n <= 0 || fm->entry_count <= 0) return;
+
+    uint64_t now = montauk::get_milliseconds();
+    if (now - fm->typeahead_time > 1000) fm->typeahead_len = 0;
+    fm->typeahead_time = now;
+    if (fm->typeahead_len == 0 && ch[0] == ' ') return;
+    if (fm->typeahead_len + n >= (int)sizeof(fm->typeahead)) return;
+    montauk::memcpy(fm->typeahead + fm->typeahead_len, ch, n);
+    fm->typeahead_len += n;
+    fm->typeahead[fm->typeahead_len] = '\0';
+
+    bool cycle = fm->typeahead_len % n == 0;
+    for (int off = n; cycle && off < fm->typeahead_len; off += n) {
+        for (int k = 0; k < n; k++) {
+            if (fm->typeahead[off + k] != ch[k]) { cycle = false; break; }
+        }
+    }
+    int prefix_len = cycle ? n : fm->typeahead_len;
+
+    int start = fm->selected < 0 ? 0 : fm->selected + (cycle ? 1 : 0);
+    for (int k = 0; k < fm->entry_count; k++) {
+        int i = (start + k) % fm->entry_count;
+        if (filemanager_prefix_match_ci(fm->entry_names[i], fm->typeahead, prefix_len)) {
+            filemanager_move_focus(win, fm, i, false);
+            return;
+        }
+    }
+}
+
 void filemanager_on_key(Window* win, const montauk::abi::KeyEvent& key) {
     FileManagerState* fm = (FileManagerState*)win->app_data;
     if (!fm || !key.pressed) return;
@@ -411,61 +508,71 @@ void filemanager_on_key(Window* win, const montauk::abi::KeyEvent& key) {
     }
 
     // ---- Keyboard shortcuts ----
-    if (key.ctrl) {
-        if (key.ascii == 'c' || key.ascii == 'C') {
-            filemanager_do_copy(fm);
+    if (key.ctrl && !key.alt) {
+        char ch = key.ascii;
+        if (ch >= 'A' && ch <= 'Z') ch += 32;
+        switch (ch) {
+        case 'c': filemanager_do_copy(fm); return;
+        case 'x': filemanager_do_cut(fm); return;
+        case 'v': filemanager_do_paste(fm); return;
+        case 'a':
+            if (filemanager_is_listing(fm)) filemanager_select_all(fm);
             return;
-        }
-        if (key.ascii == 'x' || key.ascii == 'X') {
-            filemanager_do_cut(fm);
-            return;
-        }
-        if (key.ascii == 'v' || key.ascii == 'V') {
-            filemanager_do_paste(fm);
+        case 'l': filemanager_start_pathbar(fm); return;
+        case 'n':
+            if (key.shift) filemanager_new_folder(fm);
             return;
+        default: break;
         }
     }
 
-    // F2 = rename
+    // F2 = rename, F5 = refresh
     if (key.scancode == 0x3C) {
         filemanager_start_rename(fm);
         return;
     }
+    if (key.scancode == 0x3F) {
+        filemanager_refresh(fm);
+        return;
+    }
+
+    uint8_t nav = montauk::nav_scancode(key);
+    int cur = fm->selected;
+    bool have_focus = cur >= 0 && cur < fm->entry_count;
+    int cols = fm->grid_view ? filemanager_grid_cols(win) : 1;
 
     if (key.ascii == '\b' || key.scancode == 0x0E) {
         filemanager_go_up(fm);
-    } else if (montauk::nav_scancode(key) == 0x48) {
-        // Up arrow
-        if (fm->grid_view) {
-            Rect cr_r = win->content_rect();
-            int cols = (cr_r.w - FM_SCROLLBAR_W) / FM_GRID_CELL_W;
-            if (cols < 1) cols = 1;
-            if (fm->selected >= cols) fm->selected -= cols;
-        } else {
-            if (fm->selected > 0) fm->selected--;
-        }
-        filemanager_scroll_to_selected(win, fm);
-    } else if (montauk::nav_scancode(key) == 0x50) {
-        // Down arrow
-        if (fm->grid_view) {
-            Rect cr_r = win->content_rect();
-            int cols = (cr_r.w - FM_SCROLLBAR_W) / FM_GRID_CELL_W;
-            if (cols < 1) cols = 1;
-            if (fm->selected + cols < fm->entry_count) fm->selected += cols;
-        } else {
-            if (fm->selected < fm->entry_count - 1) fm->selected++;
-        }
-        filemanager_scroll_to_selected(win, fm);
-    } else if (montauk::nav_scancode(key) == 0x4B && !key.alt && fm->grid_view) {
+    } else if (key.scancode == 0x01) {
+        // Escape: drop the selection
+        filemanager_select_single(fm, -1);
+    } else if (nav == 0x48 && !key.alt) {
+        // Up arrow (one row up in the grid)
+        int target = !have_focus ? 0 : (cur >= cols ? cur - cols : cur);
+        filemanager_move_focus(win, fm, target, key.shift);
+    } else if (nav == 0x50 && !key.alt) {
+        // Down arrow (one row down in the grid)
+        int target = !have_focus ? 0 : (cur + cols < fm->entry_count ? cur + cols : cur);
+        filemanager_move_focus(win, fm, target, key.shift);
+    } else if (nav == 0x4B && !key.alt && fm->grid_view) {
         // Left arrow (grid view only)
-        if (fm->selected > 0) fm->selected--;
-    } else if (montauk::nav_scancode(key) == 0x4D && !key.alt && fm->grid_view) {
+        filemanager_move_focus(win, fm, have_focus ? cur - 1 : 0, key.shift);
+    } else if (nav == 0x4D && !key.alt && fm->grid_view) {
         // Right arrow (grid view only)
-        if (fm->selected < fm->entry_count - 1) fm->selected++;
+        filemanager_move_focus(win, fm, have_focus ? cur + 1 : 0, key.shift);
+    } else if (nav == 0x47) {
+        // Home
+        filemanager_move_focus(win, fm, 0, key.shift);
+    } else if (nav == 0x4F) {
+        // End
+        filemanager_move_focus(win, fm, fm->entry_count - 1, key.shift);
+    } else if ((key.ascii == '\n' || key.ascii == '\r') && key.alt) {
+        // Alt+Enter: properties
+        if (have_focus) filemanager_show_selection_properties(fm, cur);
     } else if (key.ascii == '\n' || key.ascii == '\r') {
-        if (fm->selected >= 0 && fm->selected < fm->entry_count)
-            filemanager_open_entry(fm, fm->selected);
-    } else if (montauk::nav_scancode(key) == 0x53) {
+        if (have_focus && filemanager_is_entry_selected(fm, cur))
+            filemanager_open_entry(fm, cur);
+    } else if (nav == 0x53) {
         // Delete key
         filemanager_delete_selected(fm);
     } else if (key.alt && montauk::nav_scancode(key) == 0x4B) {
@@ -474,6 +581,8 @@ void filemanager_on_key(Window* win, const montauk::abi::KeyEvent& key) {
     } else if (key.alt && montauk::nav_scancode(key) == 0x4D) {
         // Alt+Right: go forward
         filemanager_go_forward(fm);
+    } else if (!key.ctrl && !key.alt) {
+        filemanager_typeahead(win, fm, key);
     }
 }
 
diff --git a/programs/src/desktop/apps/filemanager/filemanager_internal.hpp b/programs/src/desktop/apps/filemanager/filemanager_internal.hpp
index 848f6df..01d03d1 100644
--- a/programs/src/desktop/apps/filemanager/filemanager_internal.hpp
+++ b/programs/src/desktop/apps/filemanager/filemanager_internal.hpp
@@ -48,12 +48,21 @@ struct FileManagerVirtualEntry {
 // misbehaving driver and bounds memory. Far above any realistic directory.
 inline constexpr int FM_ENTRY_HARD_CAP = 8192;
 
+inline constexpr int FM_CTX_MAX_ITEMS = 10;
+
 // Single-file deletes at or below this size are freed inline; larger files go
 // to the background worker + progress dialog. Freeing a big file rewrites the
 // filesystem allocation bitmaps and can take seconds on real disks, which would
 // otherwise stall the desktop (Files runs inside desktop.elf).
 inline constexpr uint64_t FILEMANAGER_DELETE_INLINE_MAX_BYTES = 4ull * 1024 * 1024;
 
+enum FileManagerSortKey : uint8_t {
+    FM_SORT_NAME = 0,
+    FM_SORT_SIZE,
+    FM_SORT_TYPE,
+    FM_SORT_MODIFIED,
+};
+
 struct FileManagerState {
     char current_path[256];
     FileManagerLocation history[16];
@@ -67,7 +76,10 @@ struct FileManagerState {
     int64_t* entry_mtimes; // last-modified time, UTC unix seconds (0 = unknown)
     int entry_count;
     int entry_cap;         // allocated capacity of the per-entry arrays
+    // Focused entry. With no multi-selection it is also the selection; while
+    // multi_count > 0 only multi_selected marks what is selected.
     int selected;
+    int sel_anchor;     // fixed end of a Shift range selection (-1 = none)
     int scroll_offset;
     bool* is_dir;
     int last_click_item;
@@ -84,7 +96,7 @@ struct FileManagerState {
     int  clipboard_count;
     bool clipboard_is_cut;
 
-    // Multi-selection (marquee selection), sized with the entry arrays.
+    // Multi-selection (marquee, Ctrl/Shift-click), sized with the entry arrays.
     bool* multi_selected;
     int  multi_count;
 
@@ -99,7 +111,7 @@ struct FileManagerState {
     bool ctx_open;
     int ctx_x, ctx_y;
     int ctx_target_idx; // -1 = background
-    int ctx_items[8];
+    int ctx_items[FM_CTX_MAX_ITEMS];
     int ctx_item_count;
     int ctx_hover;
 
@@ -121,11 +133,22 @@ struct FileManagerState {
     FileManagerVirtualEntry* virtual_entries;
     int virtual_entry_count;
 
+    // Sort order of real directory listings (folders always come first).
+    FileManagerSortKey sort_key;
+    bool sort_desc;
+
+    // Type-to-jump: characters typed in quick succession select the first
+    // entry whose name starts with them.
+    char typeahead[32];
+    int typeahead_len;
+    uint64_t typeahead_time;
+
     // Background file operation (copy/move/delete) + its progress dialog.
     void* active_fileop; // FileOpJob*, non-null while an operation runs
 
     // File Manager-owned dialogs
     void* delete_confirm_dialog;
+    void* open_with_dialog;
 };
 
 inline constexpr int FM_TOOLBAR_H = 32;
@@ -138,6 +161,37 @@ inline constexpr int FM_GRID_CELL_H = 80;
 inline constexpr int FM_GRID_CELL_H_WRAPPED = 92;
 inline constexpr int FM_GRID_ICON = 48;
 inline constexpr int FM_GRID_PAD = 4;
+inline constexpr int FM_CTX_MENU_W = 184;
+
+// List view column layout. Columns are dropped right to left as the window
+// narrows (Modified first, then Type, then Size) so the name keeps room.
+struct FileManagerListColumns {
+    int name_x;
+    int name_right;   // right edge available to the name text
+    int modified_x;   // -1 = hidden
+    int size_x;       // -1 = hidden
+    int type_x;       // -1 = hidden
+};
+
+inline FileManagerListColumns filemanager_list_columns(int content_w) {
+    static constexpr int MIN_NAME_W = 160;
+    static constexpr int TYPE_W = 96;
+    static constexpr int SIZE_W = 76;
+    static constexpr int MODIFIED_W = 132;
+
+    FileManagerListColumns cols = {8, 0, -1, -1, -1};
+    int right = content_w - FM_SCROLLBAR_W;
+    if (right - SIZE_W >= MIN_NAME_W) { right -= SIZE_W; cols.size_x = right; }
+    if (right - TYPE_W >= MIN_NAME_W) {
+        // Type sits right of Size; shift Size left to make room.
+        cols.type_x = content_w - FM_SCROLLBAR_W - TYPE_W;
+        if (cols.size_x >= 0) cols.size_x -= TYPE_W;
+        right -= TYPE_W;
+    }
+    if (right - MODIFIED_W >= MIN_NAME_W) { right -= MODIFIED_W; cols.modified_x = right; }
+    cols.name_right = right - 8;
+    return cols;
+}
 
 // Special user folders: name, icon filename, index into DesktopState arrays
 inline constexpr int SF_COUNT = DesktopState::SPECIAL_FOLDER_COUNT;
@@ -160,6 +214,12 @@ inline constexpr int CTX_DELETE = 5;
 inline constexpr int CTX_NEW_FOLDER = 6;
 inline constexpr int CTX_PROPERTIES = 7;
 inline constexpr int CTX_REFRESH    = 8;
+inline constexpr int CTX_OPEN_WITH  = 9;
+inline constexpr int CTX_SELECT_ALL = 10;
+inline constexpr int CTX_SORT_NAME  = 11;
+inline constexpr int CTX_SORT_SIZE  = 12;
+inline constexpr int CTX_SORT_TYPE  = 13;
+inline constexpr int CTX_SORT_MODIFIED = 14;
 
 inline bool filemanager_is_virtual_view(const FileManagerState* fm) {
     return fm && fm->virtual_view != FM_VIRTUAL_VIEW_NONE;
@@ -179,6 +239,9 @@ inline const char* filemanager_virtual_view_label(FileManagerVirtualViewKind vie
 
 int special_folder_index(const char* name);
 const char* ctx_label(int action);
+const char* ctx_shortcut(const FileManagerState* fm, int action);
+// Menu items of different groups are split by a separator line.
+int ctx_group(int action);
 
 inline mtk::ContextMenuState filemanager_context_state(const FileManagerState* fm) {
     if (!fm) return {};
@@ -199,19 +262,20 @@ inline void filemanager_build_context_items(const FileManagerState* fm,
                                             int max_items) {
     if (!fm || !items || max_items <= 0) return;
     int count = fm->ctx_item_count < max_items ? fm->ctx_item_count : max_items;
-    for (int i = 0; i < count; i++)
-        items[i] = {ctx_label(fm->ctx_items[i]), fm->ctx_items[i], true};
+    for (int i = 0; i < count; i++) {
+        int action = fm->ctx_items[i];
+        items[i] = {ctx_label(action), action, true, ctx_shortcut(fm, action),
+                    i + 1 < count && ctx_group(action) != ctx_group(fm->ctx_items[i + 1])};
+    }
 }
 
 bool str_ends_with(const char* s, const char* suffix);
-bool is_image_file(const char* name);
-bool is_font_file(const char* name);
-bool is_pdf_file(const char* name);
-bool is_spreadsheet_file(const char* name);
-bool is_wordprocessor_file(const char* name);
-bool is_audio_file(const char* name);
-bool is_video_file(const char* name);
 int detect_file_type(const char* name, bool is_dir);
+// Lowercased extension after the last '.', without the dot ("" if none).
+// Leading-dot names (".profile") count as having no extension.
+void file_extension(const char* name, char* out, int out_max);
+// Human-readable type for the list view's Type column ("PDF file", "Folder").
+void filemanager_type_label(const FileManagerState* fm, int idx, char* out, int out_max);
 
 void filemanager_build_fullpath(char* out, int out_max, const char* dir, const char* name);
 const char* path_basename(const char* path);
@@ -226,6 +290,11 @@ void filemanager_free_arrays(FileManagerState* fm);
 
 void filemanager_read_drives(FileManagerState* fm);
 void filemanager_read_dir(FileManagerState* fm);
+// Re-sort a real directory listing by sort_key/sort_desc, keeping the
+// selection on the same entries. No-op for Computer and virtual views.
+void filemanager_sort_entries(FileManagerState* fm);
+// Pick a sort column: a new key sorts ascending, the current key flips order.
+void filemanager_set_sort(FileManagerState* fm, FileManagerSortKey key);
 void filemanager_free_app_icons(FileManagerState* fm);
 void filemanager_read_virtual_view(FileManagerState* fm, FileManagerVirtualViewKind view);
 void filemanager_read_apps(FileManagerState* fm);
@@ -293,6 +362,26 @@ void filemanager_commit_pathbar(FileManagerState* fm);
 
 void filemanager_open_entry(FileManagerState* fm, int idx);
 
+// ---- File associations (associations.cpp, openwith.cpp) ----
+// Default app for a file: the user's "Always use" choice from
+// <home>/config/associations.toml, else the first app (by name) whose manifest
+// lists the extension in files.types. Returns a desktop_items index or -1.
+int filemanager_assoc_default(DesktopState* ds, const char* ext);
+// Apps whose manifest claims ext come first ("recommended"); every other
+// launchable app follows. Returns the total count, *recommended gets how many
+// of those lead the list. Indices refer to ds->desktop_items.
+int filemanager_assoc_candidates(DesktopState* ds, const char* ext,
+                                 int* out, int max, int* recommended);
+// Remember item as the user's default app for ext. Returns false if ext cannot
+// be stored as a config key or the save failed.
+bool filemanager_assoc_set_default(DesktopState* ds, const char* ext, int item_index);
+// True if the file looks like text (no NULs / stray control bytes in its
+// first KiB). Empty files count as text.
+bool filemanager_file_looks_textual(const char* path);
+// Launch a desktop item with a file path argument.
+bool filemanager_launch_with(DesktopState* ds, int item_index, const char* path);
+void filemanager_show_open_with(FileManagerState* fm, int target_idx);
+
 // ---- Async file operations (copy/move/delete on a worker thread) ----
 enum FileOpKind : int {
     FILE_OP_COPY = 0,
@@ -313,6 +402,15 @@ int filemanager_grid_index_at(FileManagerState* fm, int cols, int x, int rel_y);
 
 // Selection helpers
 void filemanager_clear_multi_selection(FileManagerState* fm);
+// Replace the selection with a single entry (or none for idx < 0).
+void filemanager_select_single(FileManagerState* fm, int idx);
+// Ctrl-click: add idx to or remove it from the selection.
+void filemanager_toggle_selection(FileManagerState* fm, int idx);
+// Shift-click / Shift+arrow: select the range from sel_anchor to idx. With
+// additive set (Ctrl+Shift) the range is added to the existing selection.
+void filemanager_select_range(FileManagerState* fm, int idx, bool additive);
+void filemanager_select_all(FileManagerState* fm);
+bool filemanager_is_entry_selected(const FileManagerState* fm, int idx);
 // Fill out with selected entry indices. Returns count. Uses multi_selected if
 // non-empty, otherwise falls back to fm->selected (0 or 1 results).
 int  filemanager_collect_selection(const FileManagerState* fm, int* out, int max);
diff --git a/programs/src/desktop/apps/filemanager/filesystem.cpp b/programs/src/desktop/apps/filemanager/filesystem.cpp
index 853fda6..a2a61aa 100644
--- a/programs/src/desktop/apps/filemanager/filesystem.cpp
+++ b/programs/src/desktop/apps/filemanager/filesystem.cpp
@@ -100,6 +100,8 @@ void filemanager_free_arrays(FileManagerState* fm) {
 
 static void filemanager_reset_list_state(FileManagerState* fm) {
     fm->selected = -1;
+    fm->sel_anchor = -1;
+    fm->typeahead_len = 0;
     fm->scroll_offset = 0;
     fm->scrollbar.scroll_offset = 0;
     fm->last_click_item = -1;
@@ -344,42 +346,113 @@ void filemanager_read_dir(FileManagerState* fm) {
         if (fm->entry_count >= FM_ENTRY_HARD_CAP) break;
     }
 
-    // Sort: directories first, then alphabetical (case-insensitive)
-    for (int i = 1; i < fm->entry_count; i++) {
-        char tmp_name[128];
-        int tmp_type = fm->entry_types[i];
-        uint64_t tmp_size = fm->entry_sizes[i];
-        int64_t tmp_mtime = fm->entry_mtimes[i];
-        bool tmp_isdir = fm->is_dir[i];
-        montauk::strcpy(tmp_name, fm->entry_names[i]);
+    filemanager_reset_list_state(fm);
+    filemanager_sort_entries(fm);
+}
 
-        int j = i - 1;
-        while (j >= 0) {
-            bool swap = false;
-            if (tmp_isdir && !fm->is_dir[j]) {
-                swap = true;
-            } else if (tmp_isdir == fm->is_dir[j]) {
-                if (str_compare_ci(tmp_name, fm->entry_names[j]) < 0) {
-                    swap = true;
-                }
-            }
-            if (!swap) break;
+// Folders always lead; within each group the active column decides, with the
+// name as tie-breaker so equal sizes/types/times still list predictably.
+static int filemanager_compare_entries(const FileManagerState* fm, int a, int b) {
+    if (fm->is_dir[a] != fm->is_dir[b]) return fm->is_dir[a] ? -1 : 1;
 
-            montauk::strcpy(fm->entry_names[j + 1], fm->entry_names[j]);
-            fm->entry_types[j + 1] = fm->entry_types[j];
-            fm->entry_sizes[j + 1] = fm->entry_sizes[j];
-            fm->entry_mtimes[j + 1] = fm->entry_mtimes[j];
-            fm->is_dir[j + 1] = fm->is_dir[j];
-            j--;
-        }
-        montauk::strcpy(fm->entry_names[j + 1], tmp_name);
-        fm->entry_types[j + 1] = tmp_type;
-        fm->entry_sizes[j + 1] = tmp_size;
-        fm->entry_mtimes[j + 1] = tmp_mtime;
-        fm->is_dir[j + 1] = tmp_isdir;
+    int c = 0;
+    switch (fm->sort_key) {
+    case FM_SORT_SIZE:
+        if (fm->entry_sizes[a] != fm->entry_sizes[b])
+            c = fm->entry_sizes[a] < fm->entry_sizes[b] ? -1 : 1;
+        break;
+    case FM_SORT_MODIFIED:
+        if (fm->entry_mtimes[a] != fm->entry_mtimes[b])
+            c = fm->entry_mtimes[a] < fm->entry_mtimes[b] ? -1 : 1;
+        break;
+    case FM_SORT_TYPE: {
+        char ea[16], eb[16];
+        file_extension(fm->entry_names[a], ea, sizeof(ea));
+        file_extension(fm->entry_names[b], eb, sizeof(eb));
+        c = str_compare_ci(ea, eb);
+        break;
+    }
+    default:
+        break;
+    }
+    if (c == 0) c = str_compare_ci(fm->entry_names[a], fm->entry_names[b]);
+    return fm->sort_desc ? -c : c;
+}
+
+template <typename T>
+static void filemanager_permute(T* arr, const int* perm, int n, void* scratch) {
+    T* tmp = (T*)scratch;
+    for (int j = 0; j < n; j++) tmp[j] = arr[perm[j]];
+    montauk::memcpy(arr, tmp, (uint64_t)n * sizeof(T));
+}
+
+static int filemanager_remap_index(int idx, const int* inv, int n) {
+    return (idx >= 0 && idx < n) ? inv[idx] : idx;
+}
+
+void filemanager_sort_entries(FileManagerState* fm) {
+    if (!fm || filemanager_is_computer_view(fm) || filemanager_is_virtual_view(fm)) return;
+    int n = fm->entry_count;
+    if (n < 2) return;
+
+    // Sort an index permutation (stable bottom-up merge sort), then apply it
+    // to every parallel array once instead of swapping 128-byte names around.
+    int* perm = (int*)montauk::malloc((uint64_t)n * sizeof(int));
+    int* tmp = (int*)montauk::malloc((uint64_t)n * sizeof(int));
+    void* scratch = montauk::malloc((uint64_t)n * 128);
+    if (!perm || !tmp || !scratch) {
+        montauk::mfree(perm);
+        montauk::mfree(tmp);
+        montauk::mfree(scratch);
+        return;
     }
 
-    filemanager_reset_list_state(fm);
+    for (int i = 0; i < n; i++) perm[i] = i;
+    for (int width = 1; width < n; width *= 2) {
+        for (int lo = 0; lo < n; lo += 2 * width) {
+            int mid = lo + width < n ? lo + width : n;
+            int hi = lo + 2 * width < n ? lo + 2 * width : n;
+            int i = lo, j = mid, k = lo;
+            while (i < mid && j < hi)
+                tmp[k++] = filemanager_compare_entries(fm, perm[j], perm[i]) < 0 ? perm[j++] : perm[i++];
+            while (i < mid) tmp[k++] = perm[i++];
+            while (j < hi) tmp[k++] = perm[j++];
+        }
+        int* swap = perm; perm = tmp; tmp = swap;
+    }
+
+    auto* names = (char(*)[128])scratch;
+    for (int j = 0; j < n; j++) montauk::memcpy(names[j], fm->entry_names[perm[j]], 128);
+    montauk::memcpy(fm->entry_names, names, (uint64_t)n * 128);
+    filemanager_permute(fm->entry_types, perm, n, scratch);
+    filemanager_permute(fm->entry_sizes, perm, n, scratch);
+    filemanager_permute(fm->entry_mtimes, perm, n, scratch);
+    filemanager_permute(fm->is_dir, perm, n, scratch);
+    filemanager_permute(fm->multi_selected, perm, n, scratch);
+
+    // Keep focus, anchor and click tracking on the same entries.
+    int* inv = tmp;
+    for (int j = 0; j < n; j++) inv[perm[j]] = j;
+    fm->selected = filemanager_remap_index(fm->selected, inv, n);
+    fm->sel_anchor = filemanager_remap_index(fm->sel_anchor, inv, n);
+    fm->last_click_item = filemanager_remap_index(fm->last_click_item, inv, n);
+    fm->rename_idx = filemanager_remap_index(fm->rename_idx, inv, n);
+
+    montauk::mfree(perm);
+    montauk::mfree(tmp);
+    montauk::mfree(scratch);
+}
+
+void filemanager_set_sort(FileManagerState* fm, FileManagerSortKey key) {
+    if (!fm) return;
+    if (fm->sort_key == key) {
+        fm->sort_desc = !fm->sort_desc;
+    } else {
+        fm->sort_key = key;
+        // Largest and newest first is what one usually wants from these.
+        fm->sort_desc = key == FM_SORT_SIZE || key == FM_SORT_MODIFIED;
+    }
+    filemanager_sort_entries(fm);
 }
 
 void filemanager_free_app_icons(FileManagerState* fm) {
diff --git a/programs/src/desktop/apps/filemanager/helpers.cpp b/programs/src/desktop/apps/filemanager/helpers.cpp
index 4bf51f7..c93efbd 100644
--- a/programs/src/desktop/apps/filemanager/helpers.cpp
+++ b/programs/src/desktop/apps/filemanager/helpers.cpp
@@ -15,6 +15,91 @@ void filemanager_clear_multi_selection(FileManagerState* fm) {
     fm->multi_count = 0;
 }
 
+bool filemanager_is_entry_selected(const FileManagerState* fm, int idx) {
+    if (!fm || idx < 0 || idx >= fm->entry_count) return false;
+    if (fm->multi_count > 0) return fm->multi_selected[idx];
+    return idx == fm->selected;
+}
+
+void filemanager_select_single(FileManagerState* fm, int idx) {
+    if (!fm) return;
+    filemanager_clear_multi_selection(fm);
+    fm->selected = (idx >= 0 && idx < fm->entry_count) ? idx : -1;
+    fm->sel_anchor = fm->selected;
+}
+
+// A multi-selection of one entry collapses back to the plain single-selection
+// form, which the rename/toolbar logic treats as "one item selected".
+static void filemanager_normalize_selection(FileManagerState* fm) {
+    if (fm->multi_count != 1) return;
+    for (int i = 0; i < fm->entry_count; i++) {
+        if (fm->multi_selected[i]) {
+            filemanager_clear_multi_selection(fm);
+            fm->selected = i;
+            return;
+        }
+    }
+}
+
+// Turn a plain single selection into the multi form before extending it.
+static void filemanager_seed_multi_selection(FileManagerState* fm) {
+    if (fm->multi_count > 0) return;
+    if (fm->selected >= 0 && fm->selected < fm->entry_count) {
+        fm->multi_selected[fm->selected] = true;
+        fm->multi_count = 1;
+    }
+}
+
+void filemanager_toggle_selection(FileManagerState* fm, int idx) {
+    if (!fm || idx < 0 || idx >= fm->entry_count) return;
+    filemanager_seed_multi_selection(fm);
+
+    if (fm->multi_selected[idx]) {
+        fm->multi_selected[idx] = false;
+        fm->multi_count--;
+    } else {
+        fm->multi_selected[idx] = true;
+        fm->multi_count++;
+    }
+    fm->selected = fm->multi_count > 0 ? idx : -1;
+    fm->sel_anchor = idx;
+    filemanager_normalize_selection(fm);
+}
+
+void filemanager_select_range(FileManagerState* fm, int idx, bool additive) {
+    if (!fm || idx < 0 || idx >= fm->entry_count) return;
+
+    int anchor = fm->sel_anchor;
+    if (anchor < 0 || anchor >= fm->entry_count)
+        anchor = (fm->selected >= 0 && fm->selected < fm->entry_count) ? fm->selected : idx;
+
+    if (additive) filemanager_seed_multi_selection(fm);
+    else filemanager_clear_multi_selection(fm);
+
+    int lo = anchor < idx ? anchor : idx;
+    int hi = anchor < idx ? idx : anchor;
+    for (int i = lo; i <= hi; i++) {
+        if (!fm->multi_selected[i]) {
+            fm->multi_selected[i] = true;
+            fm->multi_count++;
+        }
+    }
+    fm->selected = idx;
+    fm->sel_anchor = anchor;
+    filemanager_normalize_selection(fm);
+}
+
+void filemanager_select_all(FileManagerState* fm) {
+    if (!fm || fm->entry_count <= 0) return;
+    if (fm->entry_count == 1) {
+        filemanager_select_single(fm, 0);
+        return;
+    }
+    for (int i = 0; i < fm->entry_count; i++) fm->multi_selected[i] = true;
+    fm->multi_count = fm->entry_count;
+    if (fm->selected < 0 || fm->selected >= fm->entry_count) fm->selected = 0;
+}
+
 int filemanager_collect_selection(const FileManagerState* fm, int* out, int max) {
     if (!fm || !out || max <= 0) return 0;
     int n = 0;
@@ -46,10 +131,64 @@ const char* ctx_label(int action) {
     case CTX_NEW_FOLDER: return "New Folder";
     case CTX_PROPERTIES: return "Properties";
     case CTX_REFRESH:    return "Refresh";
+    case CTX_OPEN_WITH:  return "Open With...";
+    case CTX_SELECT_ALL: return "Select All";
+    case CTX_SORT_NAME:  return "Sort by Name";
+    case CTX_SORT_SIZE:  return "Sort by Size";
+    case CTX_SORT_TYPE:  return "Sort by Type";
+    case CTX_SORT_MODIFIED: return "Sort by Modified";
     default:             return "?";
     }
 }
 
+const char* ctx_shortcut(const FileManagerState* fm, int action) {
+    // The active sort column shows its direction in the shortcut slot.
+    int sort_action = -1;
+    if (fm) {
+        switch (fm->sort_key) {
+        case FM_SORT_NAME:     sort_action = CTX_SORT_NAME; break;
+        case FM_SORT_SIZE:     sort_action = CTX_SORT_SIZE; break;
+        case FM_SORT_TYPE:     sort_action = CTX_SORT_TYPE; break;
+        case FM_SORT_MODIFIED: sort_action = CTX_SORT_MODIFIED; break;
+        }
+    }
+    if (action == sort_action) return fm->sort_desc ? "Desc" : "Asc";
+
+    switch (action) {
+    case CTX_OPEN:       return "Enter";
+    case CTX_COPY:       return "Ctrl+C";
+    case CTX_CUT:        return "Ctrl+X";
+    case CTX_PASTE:      return "Ctrl+V";
+    case CTX_RENAME:     return "F2";
+    case CTX_DELETE:     return "Del";
+    case CTX_NEW_FOLDER: return "Ctrl+Shift+N";
+    case CTX_PROPERTIES: return "Alt+Enter";
+    case CTX_REFRESH:    return "F5";
+    case CTX_SELECT_ALL: return "Ctrl+A";
+    default:             return nullptr;
+    }
+}
+
+int ctx_group(int action) {
+    switch (action) {
+    case CTX_OPEN:
+    case CTX_OPEN_WITH:  return 0;
+    case CTX_COPY:
+    case CTX_CUT:
+    case CTX_PASTE:      return 1;
+    case CTX_RENAME:
+    case CTX_DELETE:
+    case CTX_NEW_FOLDER: return 2;
+    case CTX_SELECT_ALL: return 3;
+    case CTX_SORT_NAME:
+    case CTX_SORT_SIZE:
+    case CTX_SORT_TYPE:
+    case CTX_SORT_MODIFIED: return 4;
+    case CTX_REFRESH:    return 5;
+    default:             return 6; // Properties
+    }
+}
+
 bool str_ends_with(const char* s, const char* suffix) {
     int slen = montauk::slen(s);
     int suflen = montauk::slen(suffix);
@@ -64,42 +203,64 @@ bool str_ends_with(const char* s, const char* suffix) {
     return true;
 }
 
-bool is_image_file(const char* name) {
-    return str_ends_with(name, ".jpg")
-        || str_ends_with(name, ".jpeg")
-        || str_ends_with(name, ".svg");
-}
-
-bool is_font_file(const char* name) {
-    return str_ends_with(name, ".ttf");
-}
-
-bool is_pdf_file(const char* name) {
-    return str_ends_with(name, ".pdf");
-}
-
-bool is_spreadsheet_file(const char* name) {
-    return str_ends_with(name, ".mss");
-}
-
-bool is_wordprocessor_file(const char* name) {
-    return str_ends_with(name, ".mwp");
-}
-
-bool is_audio_file(const char* name) {
-    return str_ends_with(name, ".mp3") || str_ends_with(name, ".wav");
-}
-
-bool is_video_file(const char* name) {
-    return str_ends_with(name, ".avi");
-}
-
 int detect_file_type(const char* name, bool is_dir) {
     if (is_dir) return 1;
     if (str_ends_with(name, ".elf")) return 2;
     return 0;
 }
 
+void file_extension(const char* name, char* out, int out_max) {
+    if (!out || out_max <= 0) return;
+    out[0] = '\0';
+    if (!name) return;
+
+    const char* dot = nullptr;
+    for (const char* p = name; *p; p++) {
+        if (*p == '.') dot = p;
+    }
+    if (!dot || dot == name || !dot[1]) return;
+
+    int n = 0;
+    for (const char* p = dot + 1; *p && n < out_max - 1; p++) {
+        char ch = *p;
+        out[n++] = (ch >= 'A' && ch <= 'Z') ? ch + 32 : ch;
+    }
+    out[n] = '\0';
+}
+
+void filemanager_type_label(const FileManagerState* fm, int idx, char* out, int out_max) {
+    if (!out || out_max <= 0) return;
+    const char* fixed = nullptr;
+    switch (fm->entry_types[idx]) {
+    case FM_ENTRY_VIRTUAL_ITEM:
+        fixed = fm->virtual_view == FM_VIRTUAL_VIEW_SYSTEM_CONFIGURATION ? "Setting" : "App";
+        break;
+    case FM_ENTRY_APPS_ROOT: fixed = "Apps"; break;
+    case FM_ENTRY_SYSTEM_CONFIGURATION_ROOT: fixed = "Settings"; break;
+    case FM_ENTRY_HOME: fixed = "Home"; break;
+    case FM_ENTRY_DRIVE: fixed = "Drive"; break;
+    case FM_ENTRY_SPECIAL_DIR:
+    case FM_ENTRY_DIR: fixed = "Folder"; break;
+    case FM_ENTRY_EXEC: fixed = "Program"; break;
+    default: break;
+    }
+    if (fixed) {
+        montauk::strncpy(out, fixed, out_max);
+        return;
+    }
+
+    char ext[16];
+    file_extension(fm->entry_names[idx], ext, 9);
+    if (!ext[0]) {
+        montauk::strncpy(out, "File", out_max);
+        return;
+    }
+    for (int k = 0; ext[k]; k++) {
+        if (ext[k] >= 'a' && ext[k] <= 'z') ext[k] -= 32;
+    }
+    snprintf(out, out_max, "%s file", ext);
+}
+
 void filemanager_build_fullpath(char* out, int out_max, const char* dir, const char* name) {
     montauk::strcpy(out, dir);
     int plen = montauk::slen(out);
diff --git a/programs/src/desktop/apps/filemanager/navigation.cpp b/programs/src/desktop/apps/filemanager/navigation.cpp
index 05b5ac3..f8a24ea 100644
--- a/programs/src/desktop/apps/filemanager/navigation.cpp
+++ b/programs/src/desktop/apps/filemanager/navigation.cpp
@@ -281,28 +281,28 @@ void filemanager_open_entry(FileManagerState* fm, int idx) {
         return;
     }
 
-    // Open file with appropriate app
+    // Open the file with its default app (see associations.cpp).
+    DesktopState* ds = fm->desktop;
+    const char* name = fm->entry_names[idx];
     char fullpath[512];
-    filemanager_build_fullpath(fullpath, 512, fm->current_path, fm->entry_names[idx]);
-    if (is_image_file(fm->entry_names[idx])) {
-        montauk::spawn("0:/apps/imageviewer/imageviewer.elf", fullpath);
-    } else if (is_font_file(fm->entry_names[idx])) {
-        montauk::spawn("0:/apps/fontpreview/fontpreview.elf", fullpath);
-    } else if (is_pdf_file(fm->entry_names[idx])) {
-        montauk::spawn("0:/apps/pdfviewer/pdfviewer.elf", fullpath);
-    } else if (is_spreadsheet_file(fm->entry_names[idx])) {
-        montauk::spawn("0:/apps/spreadsheet/spreadsheet.elf", fullpath);
-    } else if (is_wordprocessor_file(fm->entry_names[idx])) {
-        montauk::spawn("0:/apps/wordprocessor/wordprocessor.elf", fullpath);
-    } else if (is_audio_file(fm->entry_names[idx])) {
-        montauk::spawn("0:/apps/music/music.elf", fullpath);
-    } else if (is_video_file(fm->entry_names[idx])) {
-        montauk::spawn("0:/apps/video/video.elf", fullpath);
-    } else if (str_ends_with(fm->entry_names[idx], ".elf")) {
-        montauk::spawn(fullpath);
-    } else {
-        montauk::spawn("0:/apps/texteditor/texteditor.elf", fullpath);
+    filemanager_build_fullpath(fullpath, 512, fm->current_path, name);
+    if (str_ends_with(name, ".elf")) {
+        desktop_spawn_app(ds, fullpath);
+        return;
     }
+
+    char ext[16];
+    file_extension(name, ext, sizeof(ext));
+    int app = filemanager_assoc_default(ds, ext);
+    if (app >= 0 && filemanager_launch_with(ds, app, fullpath)) return;
+
+    // Nothing claims this type: text still goes straight to the Text Editor
+    // (READMEs, Makefiles, odd extensions); anything else asks.
+    if (filemanager_file_looks_textual(fullpath)) {
+        desktop_spawn_app(ds, "0:/apps/texteditor/texteditor.elf", fullpath);
+        return;
+    }
+    filemanager_show_open_with(fm, idx);
 }
 
 } // namespace filemanager
diff --git a/programs/src/desktop/apps/filemanager/render.cpp b/programs/src/desktop/apps/filemanager/render.cpp
index 7922bab..256c860 100644
--- a/programs/src/desktop/apps/filemanager/render.cpp
+++ b/programs/src/desktop/apps/filemanager/render.cpp
@@ -135,6 +135,21 @@ static void draw_marquee(Canvas& c, FileManagerState* fm, int list_y) {
     }
 }
 
+// Column title, plus a small arrow when it is the active sort column.
+static void draw_column_header(Canvas& c, int x, int header_y, const char* label,
+                               bool active, bool desc, Color color) {
+    c.text(x, header_y + 2, label, active ? colors::TEXT_COLOR : color);
+    if (!active) return;
+
+    int ax = x + text_width(label) + 6;
+    int ay = header_y + FM_HEADER_H / 2 - 2;
+    for (int r = 0; r < 4; r++) {
+        // Ascending points up, descending points down.
+        int row = desc ? 3 - r : r;
+        c.hline(ax + 3 - r, ay + row, r * 2 + 1, colors::TEXT_COLOR);
+    }
+}
+
 int filemanager_grid_row_height(FileManagerState* fm, int row, int cols) {
     if (!fm || cols <= 0 || row < 0) return FM_GRID_CELL_H;
 
@@ -342,8 +357,7 @@ void filemanager_on_draw(Window* win, Framebuffer& fb) {
             if (cell_y + row_h <= list_y || cell_y >= c.h) continue;
 
             // Selection highlight (single or multi)
-            bool cell_selected = (i == fm->selected) ||
-                                 (fm->multi_selected && fm->multi_selected[i]);
+            bool cell_selected = filemanager_is_entry_selected(fm, i);
             if (cell_selected) {
                 int sy = gui_max(cell_y, list_y);
                 int sh = gui_min(cell_y + row_h, c.h) - sy;
@@ -446,23 +460,32 @@ void filemanager_on_draw(Window* win, Framebuffer& fb) {
         int header_y = FM_TOOLBAR_H + FM_PATHBAR_H;
         c.fill_rect(0, header_y, c.w, FM_HEADER_H, Color::from_rgb(0xF8, 0xF8, 0xF8));
 
-        int name_col_x = 8;
-        int size_col_x = c.w - FM_SCROLLBAR_W - 120;
-        int type_col_x = c.w - FM_SCROLLBAR_W - 60;
+        FileManagerListColumns cols = filemanager_list_columns(c.w);
+        // Sorting only applies to real directories; Computer and the virtual
+        // views keep their curated order and show no sort arrow.
+        bool sortable = !filemanager_is_computer_view(fm) && !filemanager_is_virtual_view(fm);
 
-        c.text(name_col_x, header_y + 2, "Name", dim);
-        if (size_col_x > 100)
-            c.text(size_col_x, header_y + 2, "Size", dim);
-        if (type_col_x > 160)
-            c.text(type_col_x, header_y + 2, "Type", dim);
+        draw_column_header(c, cols.name_x, header_y, "Name",
+                           sortable && fm->sort_key == FM_SORT_NAME, fm->sort_desc, dim);
+        if (cols.modified_x >= 0)
+            draw_column_header(c, cols.modified_x, header_y, "Modified",
+                               sortable && fm->sort_key == FM_SORT_MODIFIED, fm->sort_desc, dim);
+        if (cols.size_x >= 0)
+            draw_column_header(c, cols.size_x, header_y, "Size",
+                               sortable && fm->sort_key == FM_SORT_SIZE, fm->sort_desc, dim);
+        if (cols.type_x >= 0)
+            draw_column_header(c, cols.type_x, header_y, "Type",
+                               sortable && fm->sort_key == FM_SORT_TYPE, fm->sort_desc, dim);
 
         // Header separator
         c.hline(0, header_y + FM_HEADER_H - 1, c.w, colors::BORDER);
 
         // Column separator lines
-        if (size_col_x > 100) {
-            c.vline(size_col_x - 4, header_y, c.h - header_y, colors::BORDER);
-        }
+        int first_col_x = cols.modified_x >= 0 ? cols.modified_x
+                        : cols.size_x >= 0 ? cols.size_x : cols.type_x;
+        if (first_col_x >= 0)
+            c.vline(first_col_x - 4, header_y, c.h - header_y, colors::BORDER);
+        int tz = montauk::gettz();
 
         // ---- File entries ----
         int list_y = header_y + FM_HEADER_H;
@@ -482,8 +505,7 @@ void filemanager_on_draw(Window* win, Framebuffer& fb) {
             if (iy + FM_ITEM_H <= list_y || iy >= c.h) continue;
 
             // Highlight selected (single or marquee multi-selection)
-            bool row_selected = (i == fm->selected) ||
-                                (fm->multi_selected && fm->multi_selected[i]);
+            bool row_selected = filemanager_is_entry_selected(fm, i);
             if (row_selected) {
                 int sy = gui_max(iy, list_y);
                 int sh = gui_min(iy + FM_ITEM_H, c.h) - sy;
@@ -540,7 +562,7 @@ void filemanager_on_draw(Window* win, Framebuffer& fb) {
 
             if (fm->rename_active && fm->rename_idx == i && ty >= list_y && ty + fm_sfh <= c.h) {
                 // Rename textbox inline
-                int rw = (size_col_x > 100 ? size_col_x - 8 : c.w - FM_SCROLLBAR_W - 8) - tx;
+                int rw = cols.name_right - tx;
                 c.fill_rect(tx - 2, ty - 1, rw, fm_sfh + 2, colors::WHITE);
                 c.rect(tx - 2, ty - 1, rw, fm_sfh + 2, colors::ACCENT);
                 c.text(tx, ty, fm->rename_buf, colors::TEXT_COLOR);
@@ -556,8 +578,7 @@ void filemanager_on_draw(Window* win, Framebuffer& fb) {
                 if (ty >= list_y && ty + fm_sfh <= c.h) {
                     // Truncate name to fit the name column width
                     const char* name = fm->entry_names[i];
-                    int name_max_w = size_col_x - tx - 8;
-                    if (name_max_w < 20) name_max_w = c.w - FM_SCROLLBAR_W - tx - 8;
+                    int name_max_w = cols.name_right - tx;
                     char label[64];
                     montauk::utf8::copy(label, 64, name);
 
@@ -581,28 +602,30 @@ void filemanager_on_draw(Window* win, Framebuffer& fb) {
                 }
             }
 
+            bool row_text_visible = ty >= list_y && ty + fm_sfh <= c.h;
+
+            // Modified
+            if (cols.modified_x >= 0 && row_text_visible && fm->entry_mtimes[i] > 0) {
+                char date_str[24];
+                format_datetime(date_str, sizeof(date_str), fm->entry_mtimes[i], tz);
+                c.text(cols.modified_x, ty, date_str, dim);
+            }
+
             // Size
-            if (size_col_x > 100 && !fm->is_dir[i] && ty >= list_y && ty + fm_sfh <= c.h) {
+            if (cols.size_x >= 0 && !fm->is_dir[i] && row_text_visible) {
                 char size_str[16];
                 format_size(size_str, fm->entry_sizes[i]);
-                c.text(size_col_x, ty, size_str, dim);
+                c.text(cols.size_x, ty, size_str, dim);
             }
 
             // Type
-            if (type_col_x > 160 && ty >= list_y && ty + fm_sfh <= c.h) {
-                const char* type_str = "File";
-                if (fm->entry_types[i] == FM_ENTRY_VIRTUAL_ITEM) {
-                    type_str = fm->virtual_view == FM_VIRTUAL_VIEW_SYSTEM_CONFIGURATION
-                        ? "Setting"
-                        : "App";
-                }
-                else if (fm->entry_types[i] == FM_ENTRY_APPS_ROOT) type_str = "Apps";
-                else if (fm->entry_types[i] == FM_ENTRY_SYSTEM_CONFIGURATION_ROOT) type_str = "Settings";
-                else if (fm->entry_types[i] == FM_ENTRY_HOME) type_str = "Home";
-                else if (fm->entry_types[i] == FM_ENTRY_DRIVE) type_str = "Drive";
-                else if (fm->entry_types[i] == FM_ENTRY_DIR) type_str = "Dir";
-                else if (fm->entry_types[i] == FM_ENTRY_EXEC) type_str = "Exec";
-                c.text(type_col_x, ty, type_str, dim);
+            if (cols.type_x >= 0 && row_text_visible) {
+                char type_str[24];
+                filemanager_type_label(fm, i, type_str, sizeof(type_str));
+                char type_fit[24];
+                fit_label_with_ellipsis(type_fit, sizeof(type_fit), type_str,
+                                        c.w - FM_SCROLLBAR_W - cols.type_x - 4);
+                c.text(cols.type_x, ty, type_fit, dim);
             }
         }
 
@@ -637,10 +660,10 @@ void filemanager_on_draw(Window* win, Framebuffer& fb) {
         theme.border = colors::BORDER;
         theme.text = colors::TEXT_COLOR;
 
-        mtk::ContextMenuItem items[8];
-        filemanager_build_context_items(fm, items, 8);
+        mtk::ContextMenuItem items[FM_CTX_MAX_ITEMS];
+        filemanager_build_context_items(fm, items, FM_CTX_MAX_ITEMS);
         mtk::draw_context_menu(c, filemanager_context_state(fm), items,
-                               fm->ctx_item_count, theme);
+                               fm->ctx_item_count, theme, FM_CTX_MENU_W);
     }
 }
 
diff --git a/programs/src/desktop/input.cpp b/programs/src/desktop/input.cpp
index c1e8f1c..bece980 100644
--- a/programs/src/desktop/input.cpp
+++ b/programs/src/desktop/input.cpp
@@ -887,6 +887,8 @@ void gui::desktop_handle_keyboard(DesktopState* ds, const montauk::abi::KeyEvent
     montauk::abi::KeyEvent translated_key = key;
     montauk::keyboard::translate(ds->keyboard, &translated_key);
     const montauk::abi::KeyEvent& routed_key = translated_key;
+    ds->kbd_shift_down = routed_key.shift;
+    ds->kbd_ctrl_down = routed_key.ctrl;
 
     if (ds->screen_locked) {
         handle_lock_keyboard(ds, routed_key);
diff --git a/programs/src/desktop/main.cpp b/programs/src/desktop/main.cpp
index f057cd0..58ff58a 100644
--- a/programs/src/desktop/main.cpp
+++ b/programs/src/desktop/main.cpp
@@ -181,6 +181,27 @@ void desktop_scan_apps(DesktopState* ds) {
             snprintf(item->binary_path, sizeof(item->binary_path),
                      "0:/apps/%s/%s", dirname, binary);
 
+            // File types the app opens, used by Files for default apps and
+            // "Open With". Stored lowercased as " ext1 ext2 " for whole-word
+            // matching; entries that would overflow the buffer are dropped.
+            if (auto* types = doc.get_array("files.types")) {
+                int len = 0;
+                item->file_types[len++] = ' ';
+                for (int t = 0; t < types->array.count; t++) {
+                    auto* v = types->array.items[t];
+                    if (v->type != montauk::toml::Type::String || !v->str[0]) continue;
+                    const char* ext = v->str[0] == '.' ? v->str + 1 : v->str;
+                    int elen = montauk::slen(ext);
+                    if (elen == 0 || len + elen + 2 > (int)sizeof(item->file_types)) continue;
+                    for (int k = 0; k < elen; k++) {
+                        char ch = ext[k];
+                        item->file_types[len++] = (ch >= 'A' && ch <= 'Z') ? ch + 32 : ch;
+                    }
+                    item->file_types[len++] = ' ';
+                }
+                item->file_types[len < 2 ? 0 : len] = '\0';
+            }
+
             // Load icon from app directory
             item->icon = {};
             item->icon_path[0] = '\0';
diff --git a/programs/src/fontpreview/manifest.toml b/programs/src/fontpreview/manifest.toml
index 8c54550..1314727 100644
--- a/programs/src/fontpreview/manifest.toml
+++ b/programs/src/fontpreview/manifest.toml
@@ -12,3 +12,7 @@ visible = false
 # starting directory. Don't hand it home_dir when launched from the Apps
 # folder (it would try to parse the directory path as a font).
 pass_home_dir = false
+
+[files]
+# Extensions Files opens with this app (lowercase, no dot)
+types = ["ttf"]
diff --git a/programs/src/imageviewer/manifest.toml b/programs/src/imageviewer/manifest.toml
index c23747a..640e445 100644
--- a/programs/src/imageviewer/manifest.toml
+++ b/programs/src/imageviewer/manifest.toml
@@ -6,3 +6,7 @@ icon = "image-viewer.svg"
 [menu]
 category = "Media"
 visible = false
+
+[files]
+# Extensions Files opens with this app (lowercase, no dot)
+types = ["jpg", "jpeg", "png", "bmp", "gif", "tga", "svg"]
diff --git a/programs/src/music/manifest.toml b/programs/src/music/manifest.toml
index ec3e6a3..dc37971 100644
--- a/programs/src/music/manifest.toml
+++ b/programs/src/music/manifest.toml
@@ -9,3 +9,7 @@ visible = true
 
 [launch]
 pass_home_dir = false
+
+[files]
+# Extensions Files opens with this app (lowercase, no dot)
+types = ["mp3", "wav"]
diff --git a/programs/src/pdfviewer/manifest.toml b/programs/src/pdfviewer/manifest.toml
index 236cc01..87888dd 100644
--- a/programs/src/pdfviewer/manifest.toml
+++ b/programs/src/pdfviewer/manifest.toml
@@ -6,3 +6,7 @@ icon = "pdf-viewer.svg"
 [menu]
 category = "Productivity"
 visible = false
+
+[files]
+# Extensions Files opens with this app (lowercase, no dot)
+types = ["pdf"]
diff --git a/programs/src/spreadsheet/manifest.toml b/programs/src/spreadsheet/manifest.toml
index 1690066..17c6e1a 100644
--- a/programs/src/spreadsheet/manifest.toml
+++ b/programs/src/spreadsheet/manifest.toml
@@ -6,3 +6,7 @@ icon = "spreadsheet.svg"
 [menu]
 category = "Productivity"
 visible = true
+
+[files]
+# Extensions Files opens with this app (lowercase, no dot)
+types = ["mss"]
diff --git a/programs/src/texteditor/manifest.toml b/programs/src/texteditor/manifest.toml
index a918c91..fdf51ca 100644
--- a/programs/src/texteditor/manifest.toml
+++ b/programs/src/texteditor/manifest.toml
@@ -9,3 +9,7 @@ visible = true
 
 [launch]
 pass_home_dir = false
+
+[files]
+# Extensions Files opens with this app (lowercase, no dot)
+types = ["txt", "md", "log", "toml", "ini", "cfg", "conf", "json", "xml", "csv", "c", "h", "cc", "cpp", "hpp", "rs", "s", "asm", "ld", "mk", "sh", "py", "js", "css", "html"]
diff --git a/programs/src/video/manifest.toml b/programs/src/video/manifest.toml
index 2859ca0..c932c95 100644
--- a/programs/src/video/manifest.toml
+++ b/programs/src/video/manifest.toml
@@ -6,3 +6,7 @@ icon = "video.svg"
 [menu]
 category = "Media"
 visible = true
+
+[files]
+# Extensions Files opens with this app (lowercase, no dot)
+types = ["avi"]
diff --git a/programs/src/wordprocessor/manifest.toml b/programs/src/wordprocessor/manifest.toml
index 6507d52..cb95137 100644
--- a/programs/src/wordprocessor/manifest.toml
+++ b/programs/src/wordprocessor/manifest.toml
@@ -6,3 +6,7 @@ icon = "wordprocessor.svg"
 [menu]
 category = "Productivity"
 visible = true
+
+[files]
+# Extensions Files opens with this app (lowercase, no dot)
+types = ["mwp"]