diff --git a/release/scripts/startup/bl_ui/space_outliner.py b/release/scripts/startup/bl_ui/space_outliner.py
index 5a54d4ca2d8..e0764bc990c 100644
--- a/release/scripts/startup/bl_ui/space_outliner.py
+++ b/release/scripts/startup/bl_ui/space_outliner.py
@@ -358,6 +358,10 @@ class OUTLINER_PT_filter(Panel):
         row.prop(space, "use_sync_select", text="Sync Selection")
         layout.separator()
 
+        row = layout.row(align=True)
+        row.prop(space, "show_mode_column", text="Show Mode Column")
+        layout.separator()
+
         col = layout.column(align=True)
         col.label(text="Search:")
         col.prop(space, "use_filter_complete", text="Exact Match")
diff --git a/source/blender/blenloader/intern/versioning_290.c b/source/blender/blenloader/intern/versioning_290.c
index 73a4b1a9098..cf07e9acad3 100644
--- a/source/blender/blenloader/intern/versioning_290.c
+++ b/source/blender/blenloader/intern/versioning_290.c
@@ -585,6 +585,18 @@ void blo_do_versions_290(FileData *fd, Library *UNUSED(lib), Main *bmain)
       do_versions_point_attributes(&pointcloud->pdata);
     }
 
+    /* Show outliner mode column by default. */
+    LISTBASE_FOREACH (bScreen *, screen, &bmain->screens) {
+      LISTBASE_FOREACH (ScrArea *, area, &screen->areabase) {
+        LISTBASE_FOREACH (SpaceLink *, space, &area->spacedata) {
+          if (space->spacetype == SPACE_OUTLINER) {
+            SpaceOutliner *space_outliner = (SpaceOutliner *)space;
+
+            space_outliner->flag |= SO_MODE_COLUMN;
+          }
+        }
+      }
+    }
     /* Keep this block, even when empty. */
   }
 }
diff --git a/source/blender/editors/include/UI_interface_icons.h b/source/blender/editors/include/UI_interface_icons.h
index 7b59d45b203..bbe66f7fd73 100644
--- a/source/blender/editors/include/UI_interface_icons.h
+++ b/source/blender/editors/include/UI_interface_icons.h
@@ -106,6 +106,7 @@ struct PreviewImage *UI_icon_to_preview(int icon_id);
 int UI_rnaptr_icon_get(struct bContext *C, struct PointerRNA *ptr, int rnaicon, const bool big);
 int UI_idcode_icon_get(const int idcode);
 int UI_library_icon_get(const struct ID *id);
+int UI_mode_icon_get(const int mode);
 
 #ifdef __cplusplus
 }
diff --git a/source/blender/editors/interface/interface_icons.c b/source/blender/editors/interface/interface_icons.c
index b5f902adfb5..c91b4d826a7 100644
--- a/source/blender/editors/interface/interface_icons.c
+++ b/source/blender/editors/interface/interface_icons.c
@@ -2294,6 +2294,36 @@ int UI_idcode_icon_get(const int idcode)
   }
 }
 
+int UI_mode_icon_get(const int mode)
+{
+  switch (mode) {
+    case OB_MODE_OBJECT:
+      return ICON_OBJECT_DATAMODE;
+    case OB_MODE_EDIT:
+    case OB_MODE_EDIT_GPENCIL:
+      return ICON_EDITMODE_HLT;
+    case OB_MODE_SCULPT:
+    case OB_MODE_SCULPT_GPENCIL:
+      return ICON_SCULPTMODE_HLT;
+    case OB_MODE_VERTEX_PAINT:
+    case OB_MODE_VERTEX_GPENCIL:
+      return ICON_VPAINT_HLT;
+    case OB_MODE_WEIGHT_PAINT:
+    case OB_MODE_WEIGHT_GPENCIL:
+      return ICON_WPAINT_HLT;
+    case OB_MODE_TEXTURE_PAINT:
+      return ICON_TPAINT_HLT;
+    case OB_MODE_PARTICLE_EDIT:
+      return ICON_PARTICLEMODE;
+    case OB_MODE_POSE:
+      return ICON_POSE_HLT;
+    case OB_MODE_PAINT_GPENCIL:
+      return ICON_GREASEPENCIL;
+    default:
+      return ICON_NONE;
+  }
+}
+
 /* draws icon with dpi scale factor */
 void UI_icon_draw(float x, float y, int icon_id)
 {
diff --git a/source/blender/editors/space_outliner/outliner_dragdrop.c b/source/blender/editors/space_outliner/outliner_dragdrop.c
index 94052223e39..46a5f90f6c2 100644
--- a/source/blender/editors/space_outliner/outliner_dragdrop.c
+++ b/source/blender/editors/space_outliner/outliner_dragdrop.c
@@ -893,6 +893,9 @@ static int outliner_item_drag_drop_invoke(bContext *C,
   if (outliner_item_is_co_within_close_toggle(te, view_mval[0])) {
     return (OPERATOR_CANCELLED | OPERATOR_PASS_THROUGH);
   }
+  if (outliner_is_co_within_mode_column(space_outliner, view_mval)) {
+    return OPERATOR_CANCELLED | OPERATOR_PASS_THROUGH;
+  }
 
   /* Scroll the view when dragging near edges, but not
    * when the drag goes too far outside the region. */
diff --git a/source/blender/editors/space_outliner/outliner_draw.c b/source/blender/editors/space_outliner/outliner_draw.c
index fbef3aa07d7..3de786ddd4d 100644
--- a/source/blender/editors/space_outliner/outliner_draw.c
+++ b/source/blender/editors/space_outliner/outliner_draw.c
@@ -53,6 +53,7 @@
 #include "BKE_main.h"
 #include "BKE_modifier.h"
 #include "BKE_object.h"
+#include "BKE_particle.h"
 #include "BKE_report.h"
 #include "BKE_scene.h"
 
@@ -1884,6 +1885,109 @@ static void outliner_buttons(const bContext *C,
   }
 }
 
+static void outliner_mode_toggle_fn(bContext *C, void *tselem_poin, void *UNUSED(arg2))
+{
+  SpaceOutliner *space_outliner = CTX_wm_space_outliner(C);
+  TreeStoreElem *tselem = (TreeStoreElem *)tselem_poin;
+  TreeViewContext tvc;
+  outliner_viewcontext_init(C, &tvc);
+
+  TreeElement *te = outliner_find_tree_element(&space_outliner->tree, tselem);
+  if (!te) {
+    return;
+  }
+
+  wmWindow *win = CTX_wm_window(C);
+  const bool do_extend = win->eventstate->ctrl != 0;
+  outliner_item_mode_toggle(C, &tvc, te, do_extend);
+}
+
+/* Draw icons for adding and removing objects from the current interation mode. */
+static void outliner_draw_mode_column_toggle(uiBlock *block,
+                                             TreeViewContext *tvc,
+                                             TreeElement *te,
+                                             TreeStoreElem *tselem,
+                                             const bool lock_object_modes)
+{
+  const int active_mode = tvc->obact->mode;
+  bool draw_active_icon = true;
+
+  if (tselem->type == 0 && te->idcode == ID_OB) {
+    Object *ob = (Object *)tselem->id;
+
+    /* When not locking object modes, objects can remain in non-object modes. For modes that do not
+     * allow multi-object editing, these other objects should still show be viewed as not in the
+     * mode. Otherwise multiple objects show the same mode icon in the outliner even though only
+     * one object is actually editable in the mode. */
+    if (!lock_object_modes && ob != tvc->obact && !(tvc->ob_edit || tvc->ob_pose)) {
+      draw_active_icon = false;
+    }
+
+    if (ob->type == tvc->obact->type) {
+      int icon;
+      const char *tip;
+
+      if (draw_active_icon && ob->mode == tvc->obact->mode) {
+        icon = UI_mode_icon_get(active_mode);
+        tip = TIP_("Remove from the current mode");
+      }
+      else {
+        /* Not all objects support particle systems */
+        if (active_mode == OB_MODE_PARTICLE_EDIT && !psys_get_current(ob)) {
+          return;
+        }
+        icon = ICON_DOT;
+        tip = TIP_(
+            "Change the object in the current mode\n"
+            "* Ctrl to add to the current mode");
+      }
+
+      uiBut *but = uiDefIconBut(block,
+                                UI_BTYPE_ICON_TOGGLE,
+                                0,
+                                icon,
+                                0,
+                                te->ys,
+                                UI_UNIT_X,
+                                UI_UNIT_Y,
+                                NULL,
+                                0.0,
+                                0.0,
+                                0.0,
+                                0.0,
+                                tip);
+      UI_but_func_set(but, outliner_mode_toggle_fn, tselem, NULL);
+      UI_but_flag_enable(but, UI_BUT_DRAG_LOCK);
+
+      if (ID_IS_LINKED(&ob->id)) {
+        UI_but_disable(but, TIP_("Can't edit external library data"));
+      }
+    }
+  }
+}
+
+static void outliner_draw_mode_column(const bContext *C,
+                                      uiBlock *block,
+                                      TreeViewContext *tvc,
+                                      SpaceOutliner *space_outliner,
+                                      ListBase *tree)
+{
+  TreeStoreElem *tselem;
+  const bool lock_object_modes = tvc->scene->toolsettings->object_flag & SCE_OBJECT_MODE_LOCK;
+
+  LISTBASE_FOREACH (TreeElement *, te, tree) {
+    tselem = TREESTORE(te);
+
+    if (tvc->obact && tvc->obact->mode != OB_MODE_OBJECT) {
+      outliner_draw_mode_column_toggle(block, tvc, te, tselem, lock_object_modes);
+    }
+
+    if (TSELEM_OPEN(tselem, space_outliner)) {
+      outliner_draw_mode_column(C, block, tvc, space_outliner, &te->subtree);
+    }
+  }
+}
+
 /* ****************************************************** */
 /* Normal Drawing... */
 
@@ -3500,11 +3604,20 @@ static void outliner_draw_tree(bContext *C,
                                ARegion *region,
                                SpaceOutliner *space_outliner,
                                const float restrict_column_width,
+                               const bool use_mode_column,
                                TreeElement **te_edit)
 {
   const uiFontStyle *fstyle = UI_FSTYLE_WIDGET;
   int starty, startx;
 
+  /* Move the tree a unit left in view layer mode */
+  short mode_column_offset = (use_mode_column && (space_outliner->outlinevis == SO_SCENES)) ?
+                                 UI_UNIT_X :
+                                 0;
+  if (!use_mode_column && (space_outliner->outlinevis == SO_VIEW_LAYER)) {
+    mode_column_offset -= UI_UNIT_X;
+  }
+
   GPU_blend(GPU_BLEND_ALPHA); /* Only once. */
 
   if (space_outliner->outlinevis == SO_DATA_API) {
@@ -3530,12 +3643,12 @@ static void outliner_draw_tree(bContext *C,
 
   /* Gray hierarchy lines. */
   starty = (int)region->v2d.tot.ymax - UI_UNIT_Y / 2 - OL_Y_OFFSET;
-  startx = UI_UNIT_X / 2 - (U.pixelsize + 1) / 2;
+  startx = mode_column_offset + UI_UNIT_X / 2 - (U.pixelsize + 1) / 2;
   outliner_draw_hierarchy_lines(space_outliner, &space_outliner->tree, startx, &starty);
 
   /* Items themselves. */
   starty = (int)region->v2d.tot.ymax - UI_UNIT_Y - OL_Y_OFFSET;
-  startx = 0;
+  startx = mode_column_offset;
   LISTBASE_FOREACH (TreeElement *, te, &space_outliner->tree) {
     outliner_draw_tree_element(C,
                                block,
@@ -3658,12 +3771,22 @@ void draw_outliner(const bContext *C)
   /* set matrix for 2d-view controls */
   UI_view2d_view_ortho(v2d);
 
+  /* Only show mode column in View Layers and Scenes view */
+  const bool use_mode_column = (space_outliner->flag & SO_MODE_COLUMN) &&
+                               (ELEM(space_outliner->outlinevis, SO_VIEW_LAYER, SO_SCENES));
+
   /* draw outliner stuff (background, hierarchy lines and names) */
   const float restrict_column_width = outliner_restrict_columns_width(space_outliner);
   outliner_back(region);
   block = UI_block_begin(C, region, __func__, UI_EMBOSS);
-  outliner_draw_tree(
-      (bContext *)C, block, &tvc, region, space_outliner, restrict_column_width, &te_edit);
+  outliner_draw_tree((bContext *)C,
+                     block,
+                     &tvc,
+                     region,
+                     space_outliner,
+                     restrict_column_width,
+                     use_mode_column,
+                     &te_edit);
 
   /* Compute outliner dimensions after it has been drawn. */
   int tree_width, tree_height;
@@ -3698,6 +3821,11 @@ void draw_outliner(const bContext *C)
                                props_active);
   }
 
+  /* Draw mode icons */
+  if (use_mode_column) {
+    outliner_draw_mode_column(C, block, &tvc, space_outliner, &space_outliner->tree);
+  }
+
   UI_block_emboss_set(block, UI_EMBOSS);
 
   /* Draw edit buttons if necessary. */
diff --git a/source/blender/editors/space_outliner/outliner_intern.h b/source/blender/editors/space_outliner/outliner_intern.h
index 7e7fdf4bab2..e02e6118152 100644
--- a/source/blender/editors/space_outliner/outliner_intern.h
+++ b/source/blender/editors/space_outliner/outliner_intern.h
@@ -222,7 +222,6 @@ typedef enum TreeItemSelectAction {
   OL_ITEM_ACTIVATE = (1 << 2),    /* Activate the item */
   OL_ITEM_EXTEND = (1 << 3),      /* Extend the current selection */
   OL_ITEM_RECURSIVE = (1 << 4),   /* Select recursively */
-  OL_ITEM_TOGGLE_MODE = (1 << 5)  /* Temporary */
 } TreeItemSelectAction;
 
 /* outliner_tree.c ----------------------------------------------- */
@@ -289,6 +288,12 @@ void outliner_object_mode_toggle(struct bContext *C,
 
 bool outliner_item_is_co_over_name_icons(const TreeElement *te, float view_co_x);
 bool outliner_item_is_co_within_close_toggle(const TreeElement *te, float view_co_x);
+bool outliner_is_co_within_mode_column(SpaceOutliner *space_outliner, const float view_mval[2]);
+
+void outliner_item_mode_toggle(struct bContext *C,
+                               TreeViewContext *tvc,
+                               TreeElement *te,
+                               const bool do_extend);
 
 /* outliner_edit.c ---------------------------------------------- */
 typedef void (*outliner_operation_fn)(struct bContext *C,
diff --git a/source/blender/editors/space_outliner/outliner_select.c b/source/blender/editors/space_outliner/outliner_select.c
index 266ea293d43..fe40d4cfd36 100644
--- a/source/blender/editors/space_outliner/outliner_select.c
+++ b/source/blender/editors/space_outliner/outliner_select.c
@@ -64,6 +64,7 @@
 #include "ED_undo.h"
 
 #include "WM_api.h"
+#include "WM_toolsystem.h"
 #include "WM_types.h"
 
 #include "UI_interface.h"
@@ -74,187 +75,99 @@
 
 #include "outliner_intern.h"
 
-static bool do_outliner_activate_common(bContext *C,
-                                        Main *bmain,
-                                        Depsgraph *depsgraph,
-                                        Scene *scene,
-                                        ViewLayer *view_layer,
-                                        Base *base,
-                                        const bool extend,
-                                        const bool do_exit)
-{
-  bool use_all = false;
-
-  if (do_exit) {
-    FOREACH_OBJECT_BEGIN (view_layer, ob_iter) {
-      ED_object_mode_generic_exit(bmain, depsgraph, scene, ob_iter);
-    }
-    FOREACH_OBJECT_END;
-  }
-
-  /* Just like clicking in the object changes the active object,
-   * clicking on the object data should change it as well. */
-  ED_object_base_activate(C, base);
-
-  if (extend) {
-    use_all = true;
-  }
-  else {
-    ED_object_base_deselect_all(view_layer, NULL, SEL_DESELECT);
-  }
-
-  return use_all;
-}
-
-/**
- * Bring the newly selected object into edit mode.
- *
- * If extend is used, we try to have the other compatible selected objects in the new mode as well.
- * Otherwise only the new object will be active, selected and in the edit mode.
- */
-static void do_outliner_item_editmode_toggle(
-    bContext *C, Scene *scene, ViewLayer *view_layer, Base *base, const bool extend)
+static void do_outliner_item_editmode_toggle(bContext *C, Scene *scene, Base *base)
 {
   Main *bmain = CTX_data_main(C);
-  Depsgraph *depsgraph = CTX_data_ensure_evaluated_depsgraph(C);
-  Object *obact = OBACT(view_layer);
   Object *ob = base->object;
-  bool use_all = false;
 
-  if (obact == NULL) {
-    ED_object_base_activate(C, base);
-    DEG_id_tag_update(&scene->id, ID_RECALC_SELECT);
-    WM_event_add_notifier(C, NC_SCENE | ND_OB_SELECT, scene);
-    obact = ob;
-    use_all = true;
-  }
-  else if (obact->data == ob->data) {
-    use_all = true;
-  }
-  else if (obact->mode == OB_MODE_OBJECT) {
-    use_all = do_outliner_activate_common(
-        C, bmain, depsgraph, scene, view_layer, base, extend, false);
-  }
-  else if ((ob->type != obact->type) || ((obact->mode & OB_MODE_EDIT) == 0) ||
-           ((obact->mode & OB_MODE_POSE) && ELEM(OB_ARMATURE, ob->type, obact->type)) || !extend) {
-    use_all = do_outliner_activate_common(
-        C, bmain, depsgraph, scene, view_layer, base, extend, true);
-  }
-
-  if (use_all) {
-    WM_operator_name_call(C, "OBJECT_OT_editmode_toggle", WM_OP_INVOKE_REGION_WIN, NULL);
+  if (BKE_object_is_in_editmode(ob)) {
+    ED_object_editmode_exit_ex(bmain, scene, ob, EM_FREEDATA);
+    WM_event_add_notifier(C, NC_SCENE | ND_MODE | NS_MODE_OBJECT, NULL);
   }
   else {
-    bool ok;
-    if (BKE_object_is_in_editmode(ob)) {
-      ok = ED_object_editmode_exit_ex(bmain, scene, ob, EM_FREEDATA);
-    }
-    else {
-      ok = ED_object_editmode_enter_ex(CTX_data_main(C), scene, ob, EM_NO_CONTEXT);
-    }
-    if (ok) {
-      ED_object_base_select(base, (ob->mode & OB_MODE_EDIT) ? BA_SELECT : BA_DESELECT);
-      DEG_id_tag_update(&scene->id, ID_RECALC_SELECT);
-      WM_event_add_notifier(C, NC_SCENE | ND_OB_SELECT, scene);
-    }
+    ED_object_editmode_enter_ex(CTX_data_main(C), scene, ob, EM_NO_CONTEXT);
+    WM_event_add_notifier(C, NC_SCENE | ND_MODE, NULL);
   }
 }
 
-static void do_outliner_item_posemode_toggle(
-    bContext *C, Scene *scene, ViewLayer *view_layer, Base *base, const bool extend)
+static void do_outliner_item_posemode_toggle(bContext *C, Base *base)
+{
+  Main *bmain = CTX_data_main(C);
+  Object *ob = base->object;
+
+  if (ID_IS_LINKED(ob)) {
+    BKE_report(CTX_wm_reports(C), RPT_WARNING, "Cannot pose libdata");
+  }
+  else if (ob->mode & OB_MODE_POSE) {
+    ED_object_posemode_exit_ex(bmain, ob);
+    WM_event_add_notifier(C, NC_SCENE | ND_MODE | NS_MODE_OBJECT, NULL);
+  }
+  else {
+    ED_object_posemode_enter_ex(bmain, ob);
+    WM_event_add_notifier(C, NC_SCENE | ND_MODE | NS_MODE_POSE, NULL);
+  }
+}
+
+/* Swap the current active object from the interaction mode with the given base. */
+static void do_outliner_item_mode_toggle_generic(bContext *C, TreeViewContext *tvc, Base *base)
 {
   Main *bmain = CTX_data_main(C);
   Depsgraph *depsgraph = CTX_data_ensure_evaluated_depsgraph(C);
-  Object *obact = OBACT(view_layer);
-  Object *ob = base->object;
-  bool use_all = false;
+  const int active_mode = tvc->obact->mode;
 
-  if (obact == NULL) {
+  /* Return all objects to object mode. */
+  FOREACH_OBJECT_BEGIN (tvc->view_layer, ob_iter) {
+    ED_object_mode_generic_exit(bmain, depsgraph, tvc->scene, ob_iter);
+  }
+  FOREACH_OBJECT_END;
+  WM_toolsystem_update_from_context_view3d(C);
+
+  Base *base_active = BKE_view_layer_base_find(tvc->view_layer, tvc->obact);
+  if (base_active != base) {
+    ED_object_base_select(base_active, BA_DESELECT);
     ED_object_base_activate(C, base);
-    DEG_id_tag_update(&scene->id, ID_RECALC_SELECT);
-    WM_event_add_notifier(C, NC_SCENE | ND_OB_SELECT, scene);
-    obact = ob;
-    use_all = true;
-  }
-  else if (obact->data == ob->data) {
-    use_all = true;
-  }
-  else if (obact->mode == OB_MODE_OBJECT) {
-    use_all = do_outliner_activate_common(
-        C, bmain, depsgraph, scene, view_layer, base, extend, false);
-  }
-  else if ((!ELEM(ob->type, obact->type)) ||
-           ((obact->mode & OB_MODE_EDIT) && ELEM(OB_ARMATURE, ob->type, obact->type))) {
-    use_all = do_outliner_activate_common(
-        C, bmain, depsgraph, scene, view_layer, base, extend, true);
-  }
+    ED_object_base_select(base, BA_SELECT);
 
-  if (use_all) {
-    WM_operator_name_call(C, "OBJECT_OT_posemode_toggle", WM_OP_INVOKE_REGION_WIN, NULL);
-  }
-  else {
-    bool ok = false;
-
-    if (ID_IS_LINKED(ob)) {
-      BKE_report(CTX_wm_reports(C), RPT_WARNING, "Cannot pose libdata");
-    }
-    else if (ob->mode & OB_MODE_POSE) {
-      ok = ED_object_posemode_exit_ex(bmain, ob);
-    }
-    else {
-      ok = ED_object_posemode_enter_ex(bmain, ob);
-    }
-
-    if (ok) {
-      ED_object_base_select(base, (ob->mode & OB_MODE_POSE) ? BA_SELECT : BA_DESELECT);
-
-      DEG_id_tag_update(&scene->id, ID_RECALC_SELECT);
-      WM_event_add_notifier(C, NC_SCENE | ND_MODE | NS_MODE_OBJECT, NULL);
-      WM_event_add_notifier(C, NC_SCENE | ND_OB_SELECT, scene);
-    }
+    /* XXX: Must add undo step between activation and setting mode to prevent an assert. */
+    ED_undo_push(C, "outliner mode toggle");
+    ED_object_mode_set(C, active_mode);
+    ED_outliner_select_sync_from_object_tag(C);
   }
 }
 
 /* For draw callback to run mode switching */
-void outliner_object_mode_toggle(bContext *C, Scene *scene, ViewLayer *view_layer, Base *base)
+void outliner_object_mode_toggle(bContext *UNUSED(C),
+                                 Scene *UNUSED(scene),
+                                 ViewLayer *UNUSED(view_layer),
+                                 Base *UNUSED(base))
 {
-  Object *obact = OBACT(view_layer);
-  if (obact->mode & OB_MODE_EDIT) {
-    do_outliner_item_editmode_toggle(C, scene, view_layer, base, true);
-  }
-  else if (obact->mode & OB_MODE_POSE) {
-    do_outliner_item_posemode_toggle(C, scene, view_layer, base, true);
-  }
 }
 
 /* Toggle the item's interaction mode if supported */
-static void outliner_item_mode_toggle(bContext *C,
-                                      TreeViewContext *tvc,
-                                      TreeElement *te,
-                                      const bool extend)
+void outliner_item_mode_toggle(bContext *C,
+                               TreeViewContext *tvc,
+                               TreeElement *te,
+                               const bool do_extend)
 {
   TreeStoreElem *tselem = TREESTORE(te);
 
-  if (tselem->type == 0) {
-    if (OB_DATA_SUPPORT_EDITMODE(te->idcode)) {
-      Object *ob = (Object *)outliner_search_back(te, ID_OB);
-      if ((ob != NULL) && (ob->data == tselem->id)) {
-        Base *base = BKE_view_layer_base_find(tvc->view_layer, ob);
-        if ((base != NULL) && (base->flag & BASE_VISIBLE_DEPSGRAPH)) {
-          do_outliner_item_editmode_toggle(C, tvc->scene, tvc->view_layer, base, extend);
-        }
-      }
-    }
-    else if (ELEM(te->idcode, ID_GD)) {
-      /* set grease pencil to object mode */
-      WM_operator_name_call(C, "GPENCIL_OT_editmode_toggle", WM_OP_INVOKE_REGION_WIN, NULL);
-    }
-  }
-  else if (tselem->type == TSE_POSE_BASE) {
+  if (tselem->type == 0 && te->idcode == ID_OB) {
     Object *ob = (Object *)tselem->id;
     Base *base = BKE_view_layer_base_find(tvc->view_layer, ob);
-    if (base != NULL) {
-      do_outliner_item_posemode_toggle(C, tvc->scene, tvc->view_layer, base, extend);
+
+    /* Hidden objects can be removed from the mode. */
+    if (!base || (!(base->flag & BASE_VISIBLE_DEPSGRAPH) && (ob->mode != tvc->obact->mode))) {
+      return;
+    }
+
+    if (!do_extend) {
+      do_outliner_item_mode_toggle_generic(C, tvc, base);
+    }
+    else if (tvc->ob_edit && OB_TYPE_SUPPORT_EDITMODE(ob->type)) {
+      do_outliner_item_editmode_toggle(C, tvc->scene, base);
+    }
+    else if (tvc->ob_pose && ob->type == OB_ARMATURE) {
+      do_outliner_item_posemode_toggle(C, base);
     }
   }
 }
@@ -1272,11 +1185,6 @@ void outliner_item_select(bContext *C,
                                            extend,
                                            select_flag & OL_ITEM_RECURSIVE,
                                            activate_data || space_outliner->flag & SO_SYNC_SELECT);
-
-    /* Mode toggle on data activate for now, but move later */
-    if (select_flag & OL_ITEM_TOGGLE_MODE) {
-      outliner_item_mode_toggle(C, &tvc, te, extend);
-    }
   }
 }
 
@@ -1353,6 +1261,16 @@ static bool outliner_is_co_within_restrict_columns(const SpaceOutliner *space_ou
   return (view_co_x > region->v2d.cur.xmax - outliner_restrict_columns_width(space_outliner));
 }
 
+bool outliner_is_co_within_mode_column(SpaceOutliner *space_outliner, const float view_mval[2])
+{
+  /* Mode toggles only show in View Layer and Scenes modes. */
+  if (!ELEM(space_outliner->outlinevis, SO_VIEW_LAYER, SO_SCENES)) {
+    return false;
+  }
+
+  return space_outliner->flag & SO_MODE_COLUMN && view_mval[0] < UI_UNIT_X;
+}
+
 /**
  * Action to run when clicking in the outliner,
  *
@@ -1375,6 +1293,9 @@ static int outliner_item_do_activate_from_cursor(bContext *C,
   if (outliner_is_co_within_restrict_columns(space_outliner, region, view_mval[0])) {
     return OPERATOR_CANCELLED;
   }
+  else if (outliner_is_co_within_mode_column(space_outliner, view_mval)) {
+    return OPERATOR_CANCELLED;
+  }
 
   if (!(te = outliner_find_item_at_y(space_outliner, &space_outliner->tree, view_mval[1]))) {
     if (deselect_all) {
@@ -1413,7 +1334,7 @@ static int outliner_item_do_activate_from_cursor(bContext *C,
 
       const short select_flag = OL_ITEM_ACTIVATE | (select ? OL_ITEM_SELECT : OL_ITEM_DESELECT) |
                                 (is_over_name_icons ? OL_ITEM_SELECT_DATA : 0) |
-                                (extend ? OL_ITEM_EXTEND : 0) | OL_ITEM_TOGGLE_MODE;
+                                (extend ? OL_ITEM_EXTEND : 0);
 
       outliner_item_select(C, space_outliner, activate_te, select_flag);
     }
@@ -1542,6 +1463,10 @@ static int outliner_box_select_invoke(bContext *C, wmOperator *op, const wmEvent
     return OPERATOR_CANCELLED | OPERATOR_PASS_THROUGH;
   }
 
+  if (outliner_is_co_within_mode_column(space_outliner, view_mval)) {
+    return OPERATOR_CANCELLED | OPERATOR_PASS_THROUGH;
+  }
+
   return WM_gesture_box_invoke(C, op, event);
 }
 
diff --git a/source/blender/editors/space_outliner/space_outliner.c b/source/blender/editors/space_outliner/space_outliner.c
index 6a63c3c65c3..2ed834a15dd 100644
--- a/source/blender/editors/space_outliner/space_outliner.c
+++ b/source/blender/editors/space_outliner/space_outliner.c
@@ -314,7 +314,7 @@ static SpaceLink *outliner_create(const ScrArea *UNUSED(area), const Scene *UNUS
   space_outliner->show_restrict_flags = SO_RESTRICT_ENABLE | SO_RESTRICT_HIDE;
   space_outliner->outlinevis = SO_VIEW_LAYER;
   space_outliner->sync_select_dirty |= WM_OUTLINER_SYNC_SELECT_FROM_ALL;
-  space_outliner->flag |= SO_SYNC_SELECT;
+  space_outliner->flag = SO_SYNC_SELECT | SO_MODE_COLUMN;
 
   /* header */
   region = MEM_callocN(sizeof(ARegion), "header for outliner");
diff --git a/source/blender/makesdna/DNA_space_types.h b/source/blender/makesdna/DNA_space_types.h
index 6fe6a5461e1..06ab01a9730 100644
--- a/source/blender/makesdna/DNA_space_types.h
+++ b/source/blender/makesdna/DNA_space_types.h
@@ -284,6 +284,7 @@ typedef enum eSpaceOutliner_Flag {
   /* SO_HIDE_KEYINGSETINFO = (1 << 3), */ /* UNUSED */
   SO_SKIP_SORT_ALPHA = (1 << 4),
   SO_SYNC_SELECT = (1 << 5),
+  SO_MODE_COLUMN = (1 << 6),
 } eSpaceOutliner_Flag;
 
 /* SpaceOutliner.filter */
diff --git a/source/blender/makesrna/intern/rna_space.c b/source/blender/makesrna/intern/rna_space.c
index 99f81fd531a..66d7685b3a6 100644
--- a/source/blender/makesrna/intern/rna_space.c
+++ b/source/blender/makesrna/intern/rna_space.c
@@ -3041,6 +3041,12 @@ static void rna_def_space_outliner(BlenderRNA *brna)
       prop, "Sync Outliner Selection", "Sync outliner selection with other editors");
   RNA_def_property_update(prop, NC_SPACE | ND_SPACE_OUTLINER, NULL);
 
+  prop = RNA_def_property(srna, "show_mode_column", PROP_BOOLEAN, PROP_NONE);
+  RNA_def_property_boolean_sdna(prop, NULL, "flag", SO_MODE_COLUMN);
+  RNA_def_property_ui_text(
+      prop, "Show Mode Column", "Show the mode column for mode toggle and activation");
+  RNA_def_property_update(prop, NC_SPACE | ND_SPACE_OUTLINER, NULL);
+
   /* Granular restriction column option. */
   prop = RNA_def_property(srna, "show_restrict_column_enable", PROP_BOOLEAN, PROP_NONE);
   RNA_def_property_boolean_sdna(prop, NULL, "show_restrict_flags", SO_RESTRICT_ENABLE);