diff --git a/server/datastore/mysql/in_house_apps.go b/server/datastore/mysql/in_house_apps.go
index 461447f4cb..43c3d2c97c 100644
--- a/server/datastore/mysql/in_house_apps.go
+++ b/server/datastore/mysql/in_house_apps.go
@@ -48,7 +48,7 @@ func (ds *Datastore) insertInHouseApp(ctx context.Context, payload *fleet.InHous
 		}
 		if count > 0 {
 			// ios or ipados version of this installer exists
-			err = alreadyExists("In-house app", payload.Filename)
+			return alreadyExists("in-house app", payload.Filename)
 		}
 
 		argsIos := []any{
diff --git a/server/datastore/mysql/in_house_apps_test.go b/server/datastore/mysql/in_house_apps_test.go
index 34124ff29d..cea6a6ac31 100644
--- a/server/datastore/mysql/in_house_apps_test.go
+++ b/server/datastore/mysql/in_house_apps_test.go
@@ -70,6 +70,19 @@ func testInHouseAppsCrud(t *testing.T, ds *Datastore) {
 		Version:          "1.2.3",
 	}
 
+	payloadV2 := fleet.UploadSoftwareInstallerPayload{
+		TeamID:           &team.ID,
+		UserID:           user1.ID,
+		Title:            "foo_v3_different_name", // Not used in code, needed for test
+		Filename:         "foo_v3_different_name.ipa",
+		BundleIdentifier: "com.foo",
+		StorageID:        "testingtesting456",
+		Platform:         "ios",
+		Extension:        "ipa",
+		Version:          "3.0.0",
+		ValidatedLabels:  &fleet.LabelIdentsWithScope{},
+	}
+
 	// -------------------------
 	// Upload software installer
 	_, _, err = ds.MatchOrCreateSoftwareInstaller(ctx, &payload)
@@ -102,6 +115,14 @@ func testInHouseAppsCrud(t *testing.T, ds *Datastore) {
 		return nil
 	})
 
+	// Try to upload in house app again, expect duplicate error
+	_, _, err = ds.MatchOrCreateSoftwareInstaller(ctx, &payload)
+	require.ErrorContains(t, err, fmt.Sprintf(`in-house app %q already exists`, payload.Filename))
+	// Try to upload in house app with different version or name but same bundle id
+	_, _, err = ds.MatchOrCreateSoftwareInstaller(ctx, &payloadV2)
+	require.ErrorContains(t, err, fmt.Sprintf(`in-house app %q already exists`, payloadV2.Filename))
+
+	// Get new in house app
 	installer, err := ds.GetInHouseAppMetadataByTeamAndTitleID(ctx, &team.ID, titleID)
 	require.NoError(t, err)
 	require.Equal(t, payload.Title, installer.SoftwareTitle)