diff --git a/src/core/Asset.ts b/src/core/Asset.ts
index 77e9f43..1ea3fb1 100644
--- a/src/core/Asset.ts
+++ b/src/core/Asset.ts
@@ -76,6 +76,8 @@ export class Asset
             this.children.splice(index, 1);
             asset.parent = null;
         }
+
+        asset.releaseChildrenBuffers();
     }
 
     addTransformChild(asset: Asset)
diff --git a/src/core/AssetPack.ts b/src/core/AssetPack.ts
index 89a5488..9215a32 100644
--- a/src/core/AssetPack.ts
+++ b/src/core/AssetPack.ts
@@ -203,7 +203,7 @@ export class AssetPack
         {
             if (asset.state === 'deleted')
             {
-                deleteAsset(asset);
+                deleteAssetFiles(asset);
             }
             else
             {
@@ -218,7 +218,7 @@ export class AssetPack
     }
 }
 
-async function deleteAsset(asset: Asset)
+export async function deleteAssetFiles(asset: Asset)
 {
     asset.transformChildren.forEach((child) =>
     {
diff --git a/src/core/AssetWatcher.ts b/src/core/AssetWatcher.ts
index 551b427..3bf8f7e 100644
--- a/src/core/AssetWatcher.ts
+++ b/src/core/AssetWatcher.ts
@@ -2,6 +2,7 @@ import chokidar from 'chokidar';
 import fs from 'fs-extra';
 import { Asset } from './Asset.js';
 import { AssetIgnore } from './AssetIgnore.js';
+import { deleteAssetFiles } from './AssetPack.js';
 import { Logger } from './logger/Logger.js';
 import { applySettingToAsset } from './utils/applySettingToAsset.js';
 import { path } from './utils/path.js';
@@ -222,6 +223,7 @@ export class AssetWatcher
             else if (asset.state === 'normal')
             {
                 asset.state = 'modified';
+                deleteAssetFiles(asset);
             }
 
             // flag all folders as modified..
diff --git a/src/manifest/pixiManifest.ts b/src/manifest/pixiManifest.ts
index 9f3437a..9fc4f2e 100644
--- a/src/manifest/pixiManifest.ts
+++ b/src/manifest/pixiManifest.ts
@@ -102,6 +102,8 @@ function collectAssets(
 )
 {
     if (asset.skip) return;
+    // an item may have been deleted, so we don't want to add it to the manifest!
+    if (asset.state === 'deleted') return;
 
     let localBundle = bundle;
 
diff --git a/test/core/Assetpack.test.ts b/test/core/Assetpack.test.ts
index ea9016d..e54e18c 100644
--- a/test/core/Assetpack.test.ts
+++ b/test/core/Assetpack.test.ts
@@ -2,8 +2,11 @@ import fs from 'fs-extra';
 import { existsSync } from 'node:fs';
 import { join } from 'path';
 import { describe, expect, it } from 'vitest';
+import { cacheBuster } from '../../src/cache-buster/cacheBuster.js';
 import { AssetPack } from '../../src/core/AssetPack.js';
+import { getHash } from '../../src/core/index.js';
 import { logAssetGraph } from '../../src/core/utils/logAssetGraph.js';
+import { pixiManifest } from '../../src/manifest/pixiManifest.js';
 import {
     assetPath,
     createAssetPipe,
@@ -125,6 +128,73 @@ describe('Core', () =>
         expect(fs.readJSONSync(join(outputDir, 'json.json'))).toStrictEqual({ nice: 'test' });
     });
 
+    it('should delete previously hashed versions of an asset', { timeout: 10000 }, async () =>
+    {
+        const testName = 'watch-delete-hash';
+        const inputDir = `${getInputDir(pkg, testName)}/`;
+        const outputDir = getOutputDir(pkg, testName);
+
+        createFolder(
+            pkg,
+            {
+                name: testName,
+                files: [{
+                    name: 'json.json',
+                    content: assetPath('json/json.json'),
+                }],
+                folders: [],
+            });
+
+        const testFile = join(inputDir, 'json.json');
+
+        const assetpack = new AssetPack({
+            entry: inputDir, cacheLocation: getCacheDir(pkg, testName),
+            output: outputDir,
+            cache: true,
+            pipes: [
+                cacheBuster(),
+                pixiManifest(),
+            ]
+        });
+
+        await assetpack.watch();
+
+        const origHash = getHash(join(inputDir, 'json.json'));
+
+        expect(existsSync(join(outputDir, `json-${origHash}.json`))).toBe(true);
+
+        fs.writeJSONSync(testFile, { nice: 'test' });
+
+        await new Promise((resolve) =>
+        {
+            setTimeout(resolve, 1500);
+        });
+
+        expect(existsSync(join(outputDir, `json-${origHash}.json`))).toBe(false);
+        const newHash = getHash(join(inputDir, 'json.json'));
+
+        expect(existsSync(join(outputDir, `json-${newHash}.json`))).toBe(true);
+
+        fs.removeSync(testFile);
+
+        await new Promise((resolve) =>
+        {
+            setTimeout(resolve, 1500);
+        });
+
+        await assetpack.stop();
+
+        expect(existsSync(join(outputDir, `json-${origHash}.json`))).toBe(false);
+        expect(existsSync(join(outputDir, `json-${newHash}.json`))).toBe(false);
+        expect(fs.readJSONSync(join(outputDir, 'manifest.json'))).toStrictEqual({
+            bundles: [
+                {
+                    name: 'default',
+                    assets: []
+                }]
+        });
+    });
+
     it('should ignore specified files when watching', async () =>
     {
         const testName = 'watch-ignore';