diff --git a/internal/api/resolver_mutation_gallery.go b/internal/api/resolver_mutation_gallery.go
index 55723428e..aa567734d 100644
--- a/internal/api/resolver_mutation_gallery.go
+++ b/internal/api/resolver_mutation_gallery.go
@@ -338,6 +338,10 @@ func (r *mutationResolver) GalleryDestroy(ctx context.Context, input models.Gall
 				return fmt.Errorf("gallery with id %d not found", id)
 			}
 
+			if err := gallery.LoadFiles(ctx, qb); err != nil {
+				return fmt.Errorf("loading files for gallery %d", id)
+			}
+
 			galleries = append(galleries, gallery)
 
 			imgsDestroyed, err = r.galleryService.Destroy(ctx, gallery, fileDeleter, deleteGenerated, deleteFile)
diff --git a/internal/manager/task_clean.go b/internal/manager/task_clean.go
index d2b387b8f..61076b15d 100644
--- a/internal/manager/task_clean.go
+++ b/internal/manager/task_clean.go
@@ -13,6 +13,7 @@ import (
 	"github.com/stashapp/stash/pkg/image"
 	"github.com/stashapp/stash/pkg/job"
 	"github.com/stashapp/stash/pkg/logger"
+	"github.com/stashapp/stash/pkg/models"
 	"github.com/stashapp/stash/pkg/plugin"
 	"github.com/stashapp/stash/pkg/scene"
 )
@@ -172,13 +173,13 @@ type cleanHandler struct {
 }
 
 func (h *cleanHandler) HandleFile(ctx context.Context, fileDeleter *file.Deleter, fileID file.ID) error {
-	if err := h.deleteRelatedScenes(ctx, fileDeleter, fileID); err != nil {
+	if err := h.handleRelatedScenes(ctx, fileDeleter, fileID); err != nil {
 		return err
 	}
-	if err := h.deleteRelatedGalleries(ctx, fileID); err != nil {
+	if err := h.handleRelatedGalleries(ctx, fileID); err != nil {
 		return err
 	}
-	if err := h.deleteRelatedImages(ctx, fileDeleter, fileID); err != nil {
+	if err := h.handleRelatedImages(ctx, fileDeleter, fileID); err != nil {
 		return err
 	}
 
@@ -189,7 +190,7 @@ func (h *cleanHandler) HandleFolder(ctx context.Context, fileDeleter *file.Delet
 	return h.deleteRelatedFolderGalleries(ctx, folderID)
 }
 
-func (h *cleanHandler) deleteRelatedScenes(ctx context.Context, fileDeleter *file.Deleter, fileID file.ID) error {
+func (h *cleanHandler) handleRelatedScenes(ctx context.Context, fileDeleter *file.Deleter, fileID file.ID) error {
 	mgr := GetInstance()
 	sceneQB := mgr.Database.Scene
 	scenes, err := sceneQB.FindByFileID(ctx, fileID)
@@ -225,13 +226,28 @@ func (h *cleanHandler) deleteRelatedScenes(ctx context.Context, fileDeleter *fil
 				OSHash:   oshash,
 				Path:     scene.Path,
 			}, nil)
+		} else {
+			// set the primary file to a remaining file
+			var newPrimaryID file.ID
+			for _, f := range scene.Files.List() {
+				if f.ID != fileID {
+					newPrimaryID = f.ID
+					break
+				}
+			}
+
+			if _, err := mgr.Repository.Scene.UpdatePartial(ctx, scene.ID, models.ScenePartial{
+				PrimaryFileID: &newPrimaryID,
+			}); err != nil {
+				return err
+			}
 		}
 	}
 
 	return nil
 }
 
-func (h *cleanHandler) deleteRelatedGalleries(ctx context.Context, fileID file.ID) error {
+func (h *cleanHandler) handleRelatedGalleries(ctx context.Context, fileID file.ID) error {
 	mgr := GetInstance()
 	qb := mgr.Database.Gallery
 	galleries, err := qb.FindByFileID(ctx, fileID)
@@ -255,6 +271,21 @@ func (h *cleanHandler) deleteRelatedGalleries(ctx context.Context, fileID file.I
 				Checksum: g.Checksum(),
 				Path:     g.Path,
 			}, nil)
+		} else {
+			// set the primary file to a remaining file
+			var newPrimaryID file.ID
+			for _, f := range g.Files.List() {
+				if f.Base().ID != fileID {
+					newPrimaryID = f.Base().ID
+					break
+				}
+			}
+
+			if _, err := mgr.Repository.Gallery.UpdatePartial(ctx, g.ID, models.GalleryPartial{
+				PrimaryFileID: &newPrimaryID,
+			}); err != nil {
+				return err
+			}
 		}
 	}
 
@@ -276,15 +307,16 @@ func (h *cleanHandler) deleteRelatedFolderGalleries(ctx context.Context, folderI
 		}
 
 		mgr.PluginCache.RegisterPostHooks(ctx, mgr.Database, g.ID, plugin.GalleryDestroyPost, plugin.GalleryDestroyInput{
-			Checksum: g.Checksum(),
-			Path:     g.Path,
+			// No checksum for folders
+			// Checksum: g.Checksum(),
+			Path: g.Path,
 		}, nil)
 	}
 
 	return nil
 }
 
-func (h *cleanHandler) deleteRelatedImages(ctx context.Context, fileDeleter *file.Deleter, fileID file.ID) error {
+func (h *cleanHandler) handleRelatedImages(ctx context.Context, fileDeleter *file.Deleter, fileID file.ID) error {
 	mgr := GetInstance()
 	imageQB := mgr.Database.Image
 	images, err := imageQB.FindByFileID(ctx, fileID)
@@ -312,6 +344,21 @@ func (h *cleanHandler) deleteRelatedImages(ctx context.Context, fileDeleter *fil
 				Checksum: i.Checksum,
 				Path:     i.Path,
 			}, nil)
+		} else {
+			// set the primary file to a remaining file
+			var newPrimaryID file.ID
+			for _, f := range i.Files.List() {
+				if f.Base().ID != fileID {
+					newPrimaryID = f.Base().ID
+					break
+				}
+			}
+
+			if _, err := mgr.Repository.Image.UpdatePartial(ctx, i.ID, models.ImagePartial{
+				PrimaryFileID: &newPrimaryID,
+			}); err != nil {
+				return err
+			}
 		}
 	}
 
diff --git a/internal/manager/task_export.go b/internal/manager/task_export.go
index 69bbc2d36..225938e70 100644
--- a/internal/manager/task_export.go
+++ b/internal/manager/task_export.go
@@ -335,7 +335,7 @@ func (t *ExportTask) populateGalleryImages(ctx context.Context, repo Repository)
 
 		images, err := imageReader.FindByGalleryID(ctx, g.ID)
 		if err != nil {
-			logger.Errorf("[galleries] <%s> failed to fetch images for gallery: %s", g.Checksum, err.Error())
+			logger.Errorf("[galleries] <%s> failed to fetch images for gallery: %s", g.Checksum(), err.Error())
 			continue
 		}
 
diff --git a/pkg/models/model_gallery.go b/pkg/models/model_gallery.go
index 05661d017..4da6583f8 100644
--- a/pkg/models/model_gallery.go
+++ b/pkg/models/model_gallery.go
@@ -107,9 +107,10 @@ type GalleryPartial struct {
 	CreatedAt OptionalTime
 	UpdatedAt OptionalTime
 
-	SceneIDs     *UpdateIDs
-	TagIDs       *UpdateIDs
-	PerformerIDs *UpdateIDs
+	SceneIDs      *UpdateIDs
+	TagIDs        *UpdateIDs
+	PerformerIDs  *UpdateIDs
+	PrimaryFileID *file.ID
 }
 
 func NewGalleryPartial() GalleryPartial {
diff --git a/pkg/models/model_image.go b/pkg/models/model_image.go
index 20ae370d0..377e0cc5a 100644
--- a/pkg/models/model_image.go
+++ b/pkg/models/model_image.go
@@ -121,9 +121,10 @@ type ImagePartial struct {
 	CreatedAt OptionalTime
 	UpdatedAt OptionalTime
 
-	GalleryIDs   *UpdateIDs
-	TagIDs       *UpdateIDs
-	PerformerIDs *UpdateIDs
+	GalleryIDs    *UpdateIDs
+	TagIDs        *UpdateIDs
+	PerformerIDs  *UpdateIDs
+	PrimaryFileID *file.ID
 }
 
 func NewImagePartial() ImagePartial {
diff --git a/pkg/models/model_scene.go b/pkg/models/model_scene.go
index 4057a5006..f2dfbf28d 100644
--- a/pkg/models/model_scene.go
+++ b/pkg/models/model_scene.go
@@ -143,11 +143,12 @@ type ScenePartial struct {
 	CreatedAt OptionalTime
 	UpdatedAt OptionalTime
 
-	GalleryIDs   *UpdateIDs
-	TagIDs       *UpdateIDs
-	PerformerIDs *UpdateIDs
-	MovieIDs     *UpdateMovieIDs
-	StashIDs     *UpdateStashIDs
+	GalleryIDs    *UpdateIDs
+	TagIDs        *UpdateIDs
+	PerformerIDs  *UpdateIDs
+	MovieIDs      *UpdateMovieIDs
+	StashIDs      *UpdateStashIDs
+	PrimaryFileID *file.ID
 }
 
 func NewScenePartial() ScenePartial {
diff --git a/pkg/sqlite/gallery.go b/pkg/sqlite/gallery.go
index 2c2c2682c..995f37cb8 100644
--- a/pkg/sqlite/gallery.go
+++ b/pkg/sqlite/gallery.go
@@ -246,6 +246,12 @@ func (qb *GalleryStore) UpdatePartial(ctx context.Context, id int, partial model
 		}
 	}
 
+	if partial.PrimaryFileID != nil {
+		if err := galleriesFilesTableMgr.setPrimary(ctx, id, *partial.PrimaryFileID); err != nil {
+			return nil, err
+		}
+	}
+
 	return qb.Find(ctx, id)
 }
 
diff --git a/pkg/sqlite/image.go b/pkg/sqlite/image.go
index cd37847bd..5d2eb22fd 100644
--- a/pkg/sqlite/image.go
+++ b/pkg/sqlite/image.go
@@ -193,6 +193,12 @@ func (qb *ImageStore) UpdatePartial(ctx context.Context, id int, partial models.
 		}
 	}
 
+	if partial.PrimaryFileID != nil {
+		if err := imagesFilesTableMgr.setPrimary(ctx, id, *partial.PrimaryFileID); err != nil {
+			return nil, err
+		}
+	}
+
 	return qb.find(ctx, id)
 }
 
diff --git a/pkg/sqlite/migrations/32_files.up.sql b/pkg/sqlite/migrations/32_files.up.sql
index 3644541b8..708034bd7 100644
--- a/pkg/sqlite/migrations/32_files.up.sql
+++ b/pkg/sqlite/migrations/32_files.up.sql
@@ -86,6 +86,7 @@ CREATE TABLE `images_files` (
 );
 
 CREATE INDEX `index_images_files_on_file_id` on `images_files` (`file_id`);
+CREATE UNIQUE INDEX `unique_index_images_files_on_primary` on `images_files` (`image_id`) WHERE `primary` = 1;
 
 CREATE TABLE `galleries_files` (
     `gallery_id` integer NOT NULL,
@@ -97,6 +98,7 @@ CREATE TABLE `galleries_files` (
 );
 
 CREATE INDEX `index_galleries_files_file_id` ON `galleries_files` (`file_id`);
+CREATE UNIQUE INDEX `unique_index_galleries_files_on_primary` on `galleries_files` (`gallery_id`) WHERE `primary` = 1;
 
 CREATE TABLE `scenes_files` (
     `scene_id` integer NOT NULL,
@@ -108,6 +110,7 @@ CREATE TABLE `scenes_files` (
 );
 
 CREATE INDEX `index_scenes_files_file_id` ON `scenes_files` (`file_id`);
+CREATE UNIQUE INDEX `unique_index_scenes_files_on_primary` on `scenes_files` (`scene_id`) WHERE `primary` = 1;
 
 PRAGMA foreign_keys=OFF;
 
diff --git a/pkg/sqlite/scene.go b/pkg/sqlite/scene.go
index 710e784e5..f096db130 100644
--- a/pkg/sqlite/scene.go
+++ b/pkg/sqlite/scene.go
@@ -256,6 +256,11 @@ func (qb *SceneStore) UpdatePartial(ctx context.Context, id int, partial models.
 			return nil, err
 		}
 	}
+	if partial.PrimaryFileID != nil {
+		if err := scenesFilesTableMgr.setPrimary(ctx, id, *partial.PrimaryFileID); err != nil {
+			return nil, err
+		}
+	}
 
 	return qb.Find(ctx, id)
 }
diff --git a/pkg/sqlite/table.go b/pkg/sqlite/table.go
index f4cec8244..c0b08fa6b 100644
--- a/pkg/sqlite/table.go
+++ b/pkg/sqlite/table.go
@@ -522,6 +522,28 @@ func (t *relatedFilesTable) replaceJoins(ctx context.Context, id int, fileIDs []
 	return t.insertJoins(ctx, id, firstPrimary, fileIDs)
 }
 
+func (t *relatedFilesTable) setPrimary(ctx context.Context, id int, fileID file.ID) error {
+	table := t.table.table
+
+	q := dialect.Update(table).Prepared(true).Set(goqu.Record{
+		"primary": 0,
+	}).Where(t.idColumn.Eq(id), table.Col(fileIDColumn).Neq(fileID))
+
+	if _, err := exec(ctx, q); err != nil {
+		return fmt.Errorf("unsetting primary flags in %s: %w", t.table.table.GetTable(), err)
+	}
+
+	q = dialect.Update(table).Prepared(true).Set(goqu.Record{
+		"primary": 1,
+	}).Where(t.idColumn.Eq(id), table.Col(fileIDColumn).Eq(fileID))
+
+	if _, err := exec(ctx, q); err != nil {
+		return fmt.Errorf("setting primary flag in %s: %w", t.table.table.GetTable(), err)
+	}
+
+	return nil
+}
+
 type sqler interface {
 	ToSQL() (sql string, params []interface{}, err error)
 }
diff --git a/ui/v2.5/src/components/Setup/Migrate.tsx b/ui/v2.5/src/components/Setup/Migrate.tsx
index 05f9efece..3b2226a71 100644
--- a/ui/v2.5/src/components/Setup/Migrate.tsx
+++ b/ui/v2.5/src/components/Setup/Migrate.tsx
@@ -60,7 +60,7 @@ export const Migrate: React.FC = () => {
       return;
 
     const notes = [];
-    for (let i = status.databaseSchema; i <= status.appSchema; ++i) {
+    for (let i = status.databaseSchema + 1; i <= status.appSchema; ++i) {
       const note = migrationNotes[i];
       if (note) {
         notes.push(note);