diff --git a/jest.config.ts b/jest.config.ts
index 9914401933..ed9a615897 100644
--- a/jest.config.ts
+++ b/jest.config.ts
@@ -25,7 +25,6 @@ const config: Config.InitialOptions = {
   errorOnDeprecated: true,
   // When in Continuous Integration, use only 1 worker (assuming "frugal" runner type)
   maxWorkers: env.CI === 'true' ? 1 : defaults.maxWorkers,
-  setupFilesAfterEnv: ['jest-expect-message'],
   testEnvironment: 'node',
   testMatch: ['**/?(*.)+(spec|test).ts'],
   testRunner: 'jest-circus/runner',
diff --git a/package.json b/package.json
index 026f5bbf0e..90690b0f36 100644
--- a/package.json
+++ b/package.json
@@ -27,7 +27,6 @@
     "eslint-plugin-prettier": "^4.0.0",
     "jest-circus": "^27.2.4",
     "jest-config": "^27.2.4",
-    "jest-expect-message": "^1.0.2",
     "lerna": "^4.0.0",
     "prettier": "^2.4.1",
     "standard-version": "^9.3.1",
diff --git a/packages/@jsii/kernel/package.json b/packages/@jsii/kernel/package.json
index 07f7eb6952..3a7c862a95 100644
--- a/packages/@jsii/kernel/package.json
+++ b/packages/@jsii/kernel/package.json
@@ -40,7 +40,6 @@
     "@scope/jsii-calc-lib": "^0.0.0",
     "@types/fs-extra": "^9.0.13",
     "@types/jest": "^27.0.2",
-    "@types/jest-expect-message": "^1.0.3",
     "@types/node": "^12.20.28",
     "@types/tar": "^4.0.5",
     "eslint": "^7.32.0",
diff --git a/packages/@jsii/kernel/test/kernel.test.ts b/packages/@jsii/kernel/test/kernel.test.ts
index 947ce2ffee..68eb991bac 100644
--- a/packages/@jsii/kernel/test/kernel.test.ts
+++ b/packages/@jsii/kernel/test/kernel.test.ts
@@ -579,10 +579,7 @@ defineTest(
     expect(obj2[api.TOKEN_REF]).toBeTruthy(); // verify that we received a ref as a result;
 
     const objid: string = obj2[api.TOKEN_REF];
-    expect(
-      objid.startsWith('jsii-calc.JSObjectLiteralToNativeClass@'),
-      `${objid} does not have the intended prefix`,
-    ).toBeTruthy(); // verify the type of the returned object'
+    expect(objid).toMatch(/^jsii-calc.JSObjectLiteralToNativeClass@/);
   },
 );
 
@@ -1524,12 +1521,13 @@ defineTest('ObjRefs are labeled with the "most correct" type', (sandbox) => {
       method: staticMethod,
     }).result as api.ObjRef;
 
-    expect(
-      deepEqualWithRegex(ret, typeSpec),
-      `Constructors.${staticMethod}() => ${JSON.stringify(
-        ret,
-      )}, does not match ${JSON.stringify(typeSpec)}`,
-    ).toBeTruthy();
+    if (!deepEqualWithRegex(ret, typeSpec)) {
+      throw new Error(
+        `Constructors.${staticMethod}() => ${JSON.stringify(
+          ret,
+        )}, does not match ${JSON.stringify(typeSpec)}`,
+      );
+    }
   }
 });
 
@@ -2207,7 +2205,7 @@ async function preparePackage(module: string, useCache = true) {
   }
 
   const packageRoot = findPackageRoot(module);
-  await new Promise((ok, ko) => {
+  await new Promise<void>((ok, ko) => {
     const child = childProcess.spawn('npm', ['pack', packageRoot], {
       cwd: staging,
       shell: true,
diff --git a/packages/jsii-config/package.json b/packages/jsii-config/package.json
index daeffcae08..58f7d71ad7 100644
--- a/packages/jsii-config/package.json
+++ b/packages/jsii-config/package.json
@@ -21,7 +21,6 @@
   "devDependencies": {
     "@types/inquirer": "^8.1.3",
     "@types/jest": "^27.0.2",
-    "@types/jest-expect-message": "^1.0.3",
     "@types/node": "^12.20.28",
     "@types/yargs": "^17.0.3",
     "eslint": "^7.32.0",
diff --git a/packages/jsii-diff/package.json b/packages/jsii-diff/package.json
index 724cf31a42..fe82688389 100644
--- a/packages/jsii-diff/package.json
+++ b/packages/jsii-diff/package.json
@@ -44,7 +44,6 @@
   "devDependencies": {
     "@types/fs-extra": "^9.0.13",
     "@types/jest": "^27.0.2",
-    "@types/jest-expect-message": "^1.0.3",
     "@types/node": "^12.20.28",
     "@types/tar-fs": "^2.0.1",
     "eslint": "^7.32.0",
diff --git a/packages/jsii-diff/test/util.ts b/packages/jsii-diff/test/util.ts
index 4391a5e8ea..e9442683d1 100644
--- a/packages/jsii-diff/test/util.ts
+++ b/packages/jsii-diff/test/util.ts
@@ -26,10 +26,10 @@ export async function expectError(
   expect(mms.count).not.toBe(0);
 
   const msgs = Array.from(mms.messages());
-  expect(
-    msgs.some((m) => error.test(m)),
-    `Expected error like ${error.toString()}, got ${msgs.join(', ')}`,
-  ).toBeTruthy();
+
+  if (!msgs.some((m) => error.test(m))) {
+    expect(msgs.join(',')).toMatch(error);
+  }
 }
 
 export async function compare(
diff --git a/packages/jsii/package.json b/packages/jsii/package.json
index c9033df37b..331f7210dd 100644
--- a/packages/jsii/package.json
+++ b/packages/jsii/package.json
@@ -54,7 +54,6 @@
     "@types/deep-equal": "^1.0.1",
     "@types/fs-extra": "^9.0.13",
     "@types/jest": "^27.0.2",
-    "@types/jest-expect-message": "^1.0.3",
     "@types/node": "^12.20.28",
     "@types/semver": "^7.3.8",
     "clone": "^2.1.2",