diff --git a/packages/app-lib/.sqlx/query-028eb6e4c6e87388ea7a371bd7b41e2b10c828ab93140f6d9091fbc76e03cdec.json b/packages/app-lib/.sqlx/query-028eb6e4c6e87388ea7a371bd7b41e2b10c828ab93140f6d9091fbc76e03cdec.json
new file mode 100644
index 0000000000..5329471c27
--- /dev/null
+++ b/packages/app-lib/.sqlx/query-028eb6e4c6e87388ea7a371bd7b41e2b10c828ab93140f6d9091fbc76e03cdec.json
@@ -0,0 +1,12 @@
+{
+  "db_name": "SQLite",
+  "query": "\n\t\t\t\tUPDATE instance_content_entries\n\t\t\t\tSET file_id = ?, modified_at = ?\n\t\t\t\tWHERE instance_id = ? AND file_id = ?\n\t\t\t\t",
+  "describe": {
+    "columns": [],
+    "parameters": {
+      "Right": 4
+    },
+    "nullable": []
+  },
+  "hash": "028eb6e4c6e87388ea7a371bd7b41e2b10c828ab93140f6d9091fbc76e03cdec"
+}
diff --git a/packages/app-lib/.sqlx/query-5363aa346fdead6a331a5a209d0505315b9cbb5b842216db5585cc2f7f739180.json b/packages/app-lib/.sqlx/query-5363aa346fdead6a331a5a209d0505315b9cbb5b842216db5585cc2f7f739180.json
deleted file mode 100644
index 5e44cb2188..0000000000
--- a/packages/app-lib/.sqlx/query-5363aa346fdead6a331a5a209d0505315b9cbb5b842216db5585cc2f7f739180.json
+++ /dev/null
@@ -1,20 +0,0 @@
-{
-  "db_name": "SQLite",
-  "query": "\n\t\t\t\t\t\t\t\t\t\t\t\t\tSELECT id\n\t\t\t\t\t\t\t\t\t\t\t\t\tFROM instances\n\t\t\t\t\t\t\t\t\t\t\t\t\tWHERE path = ?\n\t\t\t\t\t\t\t\t\t\t\t\t\t",
-  "describe": {
-    "columns": [
-      {
-        "name": "id",
-        "ordinal": 0,
-        "type_info": "Text"
-      }
-    ],
-    "parameters": {
-      "Right": 1
-    },
-    "nullable": [
-      false
-    ]
-  },
-  "hash": "5363aa346fdead6a331a5a209d0505315b9cbb5b842216db5585cc2f7f739180"
-}
diff --git a/packages/app-lib/.sqlx/query-7a912eb3fd9b7da37cce1d8153241aba899e679a6248c8a1de21b7b65155843e.json b/packages/app-lib/.sqlx/query-7a912eb3fd9b7da37cce1d8153241aba899e679a6248c8a1de21b7b65155843e.json
new file mode 100644
index 0000000000..f4aa8ba1ab
--- /dev/null
+++ b/packages/app-lib/.sqlx/query-7a912eb3fd9b7da37cce1d8153241aba899e679a6248c8a1de21b7b65155843e.json
@@ -0,0 +1,12 @@
+{
+  "db_name": "SQLite",
+  "query": "\n\t\t\t\tDELETE FROM instance_files\n\t\t\t\tWHERE id = ?\n\t\t\t\t",
+  "describe": {
+    "columns": [],
+    "parameters": {
+      "Right": 1
+    },
+    "nullable": []
+  },
+  "hash": "7a912eb3fd9b7da37cce1d8153241aba899e679a6248c8a1de21b7b65155843e"
+}
diff --git a/packages/app-lib/.sqlx/query-b4885df7ebd5300533179c0ed98cbca8ca982489597f413638c6af8ccbbe2bfa.json b/packages/app-lib/.sqlx/query-b4885df7ebd5300533179c0ed98cbca8ca982489597f413638c6af8ccbbe2bfa.json
new file mode 100644
index 0000000000..63e68c19be
--- /dev/null
+++ b/packages/app-lib/.sqlx/query-b4885df7ebd5300533179c0ed98cbca8ca982489597f413638c6af8ccbbe2bfa.json
@@ -0,0 +1,20 @@
+{
+  "db_name": "SQLite",
+  "query": "\n\t\tSELECT id\n\t\tFROM instance_files\n\t\tWHERE instance_id = ? AND relative_path = ?\n\t\t",
+  "describe": {
+    "columns": [
+      {
+        "name": "id",
+        "ordinal": 0,
+        "type_info": "Text"
+      }
+    ],
+    "parameters": {
+      "Right": 2
+    },
+    "nullable": [
+      false
+    ]
+  },
+  "hash": "b4885df7ebd5300533179c0ed98cbca8ca982489597f413638c6af8ccbbe2bfa"
+}
diff --git a/packages/app-lib/.sqlx/query-edab0097706c394608dbc8c65670159a6d568cb4d408876d874d218d83bc8caf.json b/packages/app-lib/.sqlx/query-edab0097706c394608dbc8c65670159a6d568cb4d408876d874d218d83bc8caf.json
new file mode 100644
index 0000000000..1b1e4e27cb
--- /dev/null
+++ b/packages/app-lib/.sqlx/query-edab0097706c394608dbc8c65670159a6d568cb4d408876d874d218d83bc8caf.json
@@ -0,0 +1,12 @@
+{
+  "db_name": "SQLite",
+  "query": "\n\t\t\t\tDELETE FROM instance_content_entries\n\t\t\t\tWHERE id IN (\n\t\t\t\t\tSELECT target_entry.id\n\t\t\t\t\tFROM instance_content_entries target_entry\n\t\t\t\t\tWHERE target_entry.instance_id = ?\n\t\t\t\t\t\tAND target_entry.file_id = ?\n\t\t\t\t\t\tAND EXISTS (\n\t\t\t\t\t\t\tSELECT 1\n\t\t\t\t\t\t\tFROM instance_content_entries source_entry\n\t\t\t\t\t\t\tWHERE source_entry.instance_id = target_entry.instance_id\n\t\t\t\t\t\t\t\tAND source_entry.content_set_id = target_entry.content_set_id\n\t\t\t\t\t\t\t\tAND source_entry.file_id = ?\n\t\t\t\t\t\t)\n\t\t\t\t)\n\t\t\t\t",
+  "describe": {
+    "columns": [],
+    "parameters": {
+      "Right": 3
+    },
+    "nullable": []
+  },
+  "hash": "edab0097706c394608dbc8c65670159a6d568cb4d408876d874d218d83bc8caf"
+}
diff --git a/packages/app-lib/src/state/instances/adapters/sqlite/content_rows.rs b/packages/app-lib/src/state/instances/adapters/sqlite/content_rows.rs
index e8b6e108a5..0a27b105cd 100644
--- a/packages/app-lib/src/state/instances/adapters/sqlite/content_rows.rs
+++ b/packages/app-lib/src/state/instances/adapters/sqlite/content_rows.rs
@@ -619,6 +619,83 @@ pub(crate) async fn rename_instance_file(
 ) -> crate::Result<Option<InstanceFile>> {
     let enabled = i64::from(enabled);
     let modified_at = Utc::now().timestamp();
+    let mut tx = pool.begin().await?;
+
+    let source_id = sqlx::query_scalar!(
+        "
+		SELECT id
+		FROM instance_files
+		WHERE instance_id = ? AND relative_path = ?
+		",
+        instance_id,
+        old_relative_path,
+    )
+    .fetch_optional(&mut *tx)
+    .await?;
+    let target_id = sqlx::query_scalar!(
+        "
+		SELECT id
+		FROM instance_files
+		WHERE instance_id = ? AND relative_path = ?
+		",
+        instance_id,
+        new_relative_path,
+    )
+    .fetch_optional(&mut *tx)
+    .await?;
+
+    if let (Some(source_id), Some(target_id)) =
+        (source_id.as_deref(), target_id.as_deref())
+        && source_id != target_id
+    {
+        sqlx::query!(
+            "
+				DELETE FROM instance_content_entries
+				WHERE id IN (
+					SELECT target_entry.id
+					FROM instance_content_entries target_entry
+					WHERE target_entry.instance_id = ?
+						AND target_entry.file_id = ?
+						AND EXISTS (
+							SELECT 1
+							FROM instance_content_entries source_entry
+							WHERE source_entry.instance_id = target_entry.instance_id
+								AND source_entry.content_set_id = target_entry.content_set_id
+								AND source_entry.file_id = ?
+						)
+				)
+				",
+            instance_id,
+            target_id,
+            source_id,
+        )
+        .execute(&mut *tx)
+        .await?;
+
+        sqlx::query!(
+            "
+				UPDATE instance_content_entries
+				SET file_id = ?, modified_at = ?
+				WHERE instance_id = ? AND file_id = ?
+				",
+            source_id,
+            modified_at,
+            instance_id,
+            target_id,
+        )
+        .execute(&mut *tx)
+        .await?;
+
+        sqlx::query!(
+            "
+				DELETE FROM instance_files
+				WHERE id = ?
+				",
+            target_id,
+        )
+        .execute(&mut *tx)
+        .await?;
+    }
 
     sqlx::query!(
         "
@@ -638,9 +715,11 @@ pub(crate) async fn rename_instance_file(
         instance_id,
         old_relative_path,
     )
-    .execute(pool)
+    .execute(&mut *tx)
     .await?;
 
+    tx.commit().await?;
+
     get_instance_file_by_relative_path(instance_id, new_relative_path, pool)
         .await
 }