diff --git a/.changeset/tame-squids-fail.md b/.changeset/tame-squids-fail.md
new file mode 100644
index 000000000..cdd055daa
--- /dev/null
+++ b/.changeset/tame-squids-fail.md
@@ -0,0 +1,5 @@
+---
+"@headstartwp/next": patch
+---
+
+Fix an annoying bug that would require deleting the .next/cache folder after change headless.config.js or .env files
diff --git a/package-lock.json b/package-lock.json
index 252c2ae04..300851db5 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -21836,6 +21836,111 @@
       "engines": {
         "node": ">=16.0.0"
       }
+    },
+    "node_modules/@next/swc-darwin-arm64": {
+      "version": "13.4.4",
+      "resolved": "https://registry.npmjs.org/@next/swc-darwin-arm64/-/swc-darwin-arm64-13.4.4.tgz",
+      "integrity": "sha512-xfjgXvp4KalNUKZMHmsFxr1Ug+aGmmO6NWP0uoh4G3WFqP/mJ1xxfww0gMOeMeSq/Jyr5k7DvoZ2Pv+XOITTtw==",
+      "cpu": [
+        "arm64"
+      ],
+      "optional": true,
+      "os": [
+        "darwin"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@next/swc-darwin-x64": {
+      "version": "13.4.4",
+      "resolved": "https://registry.npmjs.org/@next/swc-darwin-x64/-/swc-darwin-x64-13.4.4.tgz",
+      "integrity": "sha512-ZY9Ti1hkIwJsxGus3nlubIkvYyB0gNOYxKrfsOrLEqD0I2iCX8D7w8v6QQZ2H+dDl6UT29oeEUdDUNGk4UEpfg==",
+      "cpu": [
+        "x64"
+      ],
+      "optional": true,
+      "os": [
+        "darwin"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@next/swc-linux-arm64-gnu": {
+      "version": "13.4.4",
+      "resolved": "https://registry.npmjs.org/@next/swc-linux-arm64-gnu/-/swc-linux-arm64-gnu-13.4.4.tgz",
+      "integrity": "sha512-+KZnDeMShYkpkqAvGCEDeqYTRADJXc6SY1jWXz+Uo6qWQO/Jd9CoyhTJwRSxvQA16MoYzvILkGaDqirkRNctyA==",
+      "cpu": [
+        "arm64"
+      ],
+      "optional": true,
+      "os": [
+        "linux"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@next/swc-linux-arm64-musl": {
+      "version": "13.4.4",
+      "resolved": "https://registry.npmjs.org/@next/swc-linux-arm64-musl/-/swc-linux-arm64-musl-13.4.4.tgz",
+      "integrity": "sha512-evC1twrny2XDT4uOftoubZvW3EG0zs0ZxMwEtu/dDGVRO5n5pT48S8qqEIBGBUZYu/Xx4zzpOkIxx1vpWdE+9A==",
+      "cpu": [
+        "arm64"
+      ],
+      "optional": true,
+      "os": [
+        "linux"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@next/swc-win32-arm64-msvc": {
+      "version": "13.4.4",
+      "resolved": "https://registry.npmjs.org/@next/swc-win32-arm64-msvc/-/swc-win32-arm64-msvc-13.4.4.tgz",
+      "integrity": "sha512-FP8AadgSq4+HPtim7WBkCMGbhr5vh9FePXiWx9+YOdjwdQocwoCK5ZVC3OW8oh3TWth6iJ0AXJ/yQ1q1cwSZ3A==",
+      "cpu": [
+        "arm64"
+      ],
+      "optional": true,
+      "os": [
+        "win32"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@next/swc-win32-ia32-msvc": {
+      "version": "13.4.4",
+      "resolved": "https://registry.npmjs.org/@next/swc-win32-ia32-msvc/-/swc-win32-ia32-msvc-13.4.4.tgz",
+      "integrity": "sha512-3WekVmtuA2MCdcAOrgrI+PuFiFURtSyyrN1I3UPtS0ckR2HtLqyqmS334Eulf15g1/bdwMteePdK363X/Y9JMg==",
+      "cpu": [
+        "ia32"
+      ],
+      "optional": true,
+      "os": [
+        "win32"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
+    },
+    "node_modules/@next/swc-win32-x64-msvc": {
+      "version": "13.4.4",
+      "resolved": "https://registry.npmjs.org/@next/swc-win32-x64-msvc/-/swc-win32-x64-msvc-13.4.4.tgz",
+      "integrity": "sha512-AHRITu/CrlQ+qzoqQtEMfaTu7GHaQ6bziQln/pVWpOYC1wU+Mq6VQQFlsDtMCnDztPZtppAXdvvbNS7pcfRzlw==",
+      "cpu": [
+        "x64"
+      ],
+      "optional": true,
+      "os": [
+        "win32"
+      ],
+      "engines": {
+        "node": ">= 10"
+      }
     }
   }
 }
diff --git a/packages/next/src/config/withHeadlessConfig.ts b/packages/next/src/config/withHeadlessConfig.ts
index 81518a58b..bcd5ab039 100644
--- a/packages/next/src/config/withHeadlessConfig.ts
+++ b/packages/next/src/config/withHeadlessConfig.ts
@@ -158,16 +158,29 @@ export function withHeadlessConfig(
 				setHeadstartWPConfig(${JSON.stringify(headlessConfig)});
 			`;
 
+			// clear webpack cache whenever headless.config.js changes or one of the env files
 			if (Array.isArray(config.cache.buildDependencies.config)) {
 				const [nextConfigPath] = config.cache.buildDependencies.config;
 
 				const headlessConfigPath = path.resolve(nextConfigPath, '../headless.config.js');
+				const envLocalPath = path.resolve(nextConfigPath, '../.env.local');
+				const envPath = path.resolve(nextConfigPath, '../.env');
+				const envDevPath = path.resolve(nextConfigPath, '../.env.development');
 
 				if (fs.existsSync(headlessConfigPath)) {
 					config.cache.buildDependencies.config.push(headlessConfigPath);
-					config.cache.buildDependencies.config.push(
-						path.resolve(nextConfigPath, '../.env.local'),
-					);
+				}
+
+				if (fs.existsSync(envLocalPath)) {
+					config.cache.buildDependencies.config.push(envLocalPath);
+				}
+
+				if (fs.existsSync(envPath)) {
+					config.cache.buildDependencies.config.push(envPath);
+				}
+
+				if (fs.existsSync(envDevPath)) {
+					config.cache.buildDependencies.config.push(envDevPath);
 				}
 			}