diff --git a/doc/api/assert.md b/doc/api/assert.md
index 32b462fbfc..7d384c215b 100644
--- a/doc/api/assert.md
+++ b/doc/api/assert.md
@@ -39,6 +39,27 @@ strict methods. For example, [`assert.deepEqual()`][] will behave like
 In strict assertion mode, error messages for objects display a diff. In legacy
 assertion mode, error messages for objects display the objects, often truncated.
 
+### Message parameter semantics
+
+For assertion methods that accept an optional `message` parameter, the message
+may be provided in one of the following forms:
+
+* **string**: Used as-is. If additional arguments are supplied after the
+  `message` string, they are treated as printf-like substitutions (see
+  [`util.format()`][]).
+* **Error**: If an `Error` instance is provided as `message`, that error is
+  thrown directly instead of an `AssertionError`.
+* **function**: A function of the form `(actual, expected) => string`. It is
+  called only when the assertion fails and should return a string to be used as
+  the error message. Non-string return values are ignored and the default
+  message is used instead.
+
+If additional arguments are passed along with an `Error` or a function as
+`message`, the call is rejected with `ERR_AMBIGUOUS_ARGUMENT`.
+
+If the first item is neither a string, `Error`, nor function, `ERR_INVALID_ARG_TYPE`
+is thrown.
+
 To use strict assertion mode:
 
 ```mjs
@@ -305,10 +326,14 @@ destructuring and call methods directly on the instance.
 
 <!-- YAML
 added: v0.5.9
+changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
 -->
 
 * `value` {any} The input that is checked for being truthy.
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 An alias of [`assert.ok()`][].
 
@@ -324,6 +349,9 @@ changes:
   - version: v25.0.0
     pr-url: https://github.com/nodejs/node/pull/57627
     description: Invalid dates are now considered equal.
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version: v24.0.0
     pr-url: https://github.com/nodejs/node/pull/57622
     description: Recursion now stops when either side encounters a circular
@@ -375,7 +403,7 @@ changes:
 
 * `actual` {any}
 * `expected` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 **Strict assertion mode**
 
@@ -524,6 +552,9 @@ changes:
   - version: v25.0.0
     pr-url: https://github.com/nodejs/node/pull/57627
     description: Invalid dates are now considered equal.
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version: v24.0.0
     pr-url: https://github.com/nodejs/node/pull/57622
     description: Recursion now stops when either side encounters a circular
@@ -567,7 +598,7 @@ changes:
 
 * `actual` {any}
 * `expected` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 Tests for deep equality between the `actual` and `expected` parameters.
 "Deep" equality means that the enumerable "own" properties of child objects
@@ -829,6 +860,9 @@ added:
   - v13.6.0
   - v12.16.0
 changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version: v16.0.0
     pr-url: https://github.com/nodejs/node/pull/38111
     description: This API is no longer experimental.
@@ -836,7 +870,7 @@ changes:
 
 * `string` {string}
 * `regexp` {RegExp}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 Expects the `string` input not to match the regular expression.
 
@@ -1069,6 +1103,9 @@ assert.doesNotThrow(
 <!-- YAML
 added: v0.1.21
 changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version:
       - v16.0.0
       - v14.18.0
@@ -1083,7 +1120,7 @@ changes:
 
 * `actual` {any}
 * `expected` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 **Strict assertion mode**
 
@@ -1254,6 +1291,9 @@ added:
   - v13.6.0
   - v12.16.0
 changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version: v16.0.0
     pr-url: https://github.com/nodejs/node/pull/38111
     description: This API is no longer experimental.
@@ -1261,7 +1301,7 @@ changes:
 
 * `string` {string}
 * `regexp` {RegExp}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 Expects the `string` input to match the regular expression.
 
@@ -1303,6 +1343,9 @@ instance of {Error} then it will be thrown instead of the
 <!-- YAML
 added: v0.1.21
 changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version:
       - v16.0.0
       - v14.18.0
@@ -1338,7 +1381,7 @@ changes:
 
 * `actual` {any}
 * `expected` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 **Strict assertion mode**
 
@@ -1427,6 +1470,9 @@ instead of the `AssertionError`.
 <!-- YAML
 added: v1.2.0
 changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version: v9.0.0
     pr-url: https://github.com/nodejs/node/pull/15398
     description: The `-0` and `+0` are not considered equal anymore.
@@ -1458,7 +1504,7 @@ changes:
 
 * `actual` {any}
 * `expected` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 Tests for deep strict inequality. Opposite of [`assert.deepStrictEqual()`][].
 
@@ -1487,6 +1533,9 @@ instead of the [`AssertionError`][].
 <!-- YAML
 added: v0.1.21
 changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version:
       - v16.0.0
       - v14.18.0
@@ -1501,7 +1550,7 @@ changes:
 
 * `actual` {any}
 * `expected` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 **Strict assertion mode**
 
@@ -1551,6 +1600,9 @@ parameter is an instance of {Error} then it will be thrown instead of the
 <!-- YAML
 added: v0.1.21
 changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version: v10.0.0
     pr-url: https://github.com/nodejs/node/pull/17003
     description: Used comparison changed from Strict Equality to `Object.is()`.
@@ -1558,7 +1610,7 @@ changes:
 
 * `actual` {any}
 * `expected` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 Tests strict inequality between the `actual` and `expected` parameters as
 determined by [`Object.is()`][].
@@ -1604,6 +1656,9 @@ instead of the `AssertionError`.
 <!-- YAML
 added: v0.1.21
 changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version: v10.0.0
     pr-url: https://github.com/nodejs/node/pull/18319
     description: The `assert.ok()` (no arguments) will now use a predefined
@@ -1611,7 +1666,7 @@ changes:
 -->
 
 * `value` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 Tests if `value` is truthy. It is equivalent to
 `assert.equal(!!value, true, message)`.
@@ -1844,6 +1899,9 @@ argument gets considered.
 <!-- YAML
 added: v0.1.21
 changes:
+  - version: REPLACEME
+    pr-url: https://github.com/nodejs/node/pull/58849
+    description: Message may now be a `printf`-like format string or function.
   - version: v10.0.0
     pr-url: https://github.com/nodejs/node/pull/17003
     description: Used comparison changed from Strict Equality to `Object.is()`.
@@ -1851,7 +1909,14 @@ changes:
 
 * `actual` {any}
 * `expected` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function} Postfix `printf`-like arguments in case
+  it's used as format string.
+  If message is a function, it is called in case of a comparison failure. The
+  function receives the `actual` and `expected` arguments and has to return a
+  string that is going to be used as error message.
+  `printf`-like format strings and functions are beneficial for performance
+  reasons in case arguments are passed through. In addition, it allows nice
+  formatting with ease.
 
 Tests strict equality between the `actual` and `expected` parameters as
 determined by [`Object.is()`][].
@@ -1880,8 +1945,17 @@ const oranges = 2;
 assert.strictEqual(apples, oranges, `apples ${apples} !== oranges ${oranges}`);
 // AssertionError [ERR_ASSERTION]: apples 1 !== oranges 2
 
+assert.strictEqual(apples, oranges, 'apples %s !== oranges %s', apples, oranges);
+// AssertionError [ERR_ASSERTION]: apples 1 !== oranges 2
+
 assert.strictEqual(1, '1', new TypeError('Inputs are not identical'));
 // TypeError: Inputs are not identical
+
+assert.strictEqual(apples, oranges, (actual, expected) => {
+  // Do 'heavy' computations
+  return `I expected ${expected} but I got ${actual}`;
+});
+// AssertionError [ERR_ASSERTION]: I expected oranges but I got apples
 ```
 
 ```cjs
@@ -1908,8 +1982,17 @@ const oranges = 2;
 assert.strictEqual(apples, oranges, `apples ${apples} !== oranges ${oranges}`);
 // AssertionError [ERR_ASSERTION]: apples 1 !== oranges 2
 
+assert.strictEqual(apples, oranges, 'apples %s !== oranges %s', apples, oranges);
+// AssertionError [ERR_ASSERTION]: apples 1 !== oranges 2
+
 assert.strictEqual(1, '1', new TypeError('Inputs are not identical'));
 // TypeError: Inputs are not identical
+
+assert.strictEqual(apples, oranges, (actual, expected) => {
+  // Do 'heavy' computations
+  return `I expected ${expected} but I got ${actual}`;
+});
+// AssertionError [ERR_ASSERTION]: I expected oranges but I got apples
 ```
 
 If the values are not strictly equal, an [`AssertionError`][] is thrown with a
@@ -2295,7 +2378,7 @@ changes:
 
 * `actual` {any}
 * `expected` {any}
-* `message` {string|Error}
+* `message` {string|Error|Function}
 
 Tests for partial deep equality between the `actual` and `expected` parameters.
 "Deep" equality means that the enumerable "own" properties of child objects
@@ -2460,5 +2543,6 @@ assert.partialDeepStrictEqual(
 [`assert.strictEqual()`]: #assertstrictequalactual-expected-message
 [`assert.throws()`]: #assertthrowsfn-error-message
 [`getColorDepth()`]: tty.md#writestreamgetcolordepthenv
+[`util.format()`]: util.md#utilformatformat-args
 [enumerable "own" properties]: https://developer.mozilla.org/en-US/docs/Web/JavaScript/Enumerability_and_ownership_of_properties
 [prototype-spec]: https://tc39.github.io/ecma262/#sec-ordinary-object-internal-methods-and-internal-slots
diff --git a/lib/assert.js b/lib/assert.js
index 6dc0694a17..e4be22da54 100644
--- a/lib/assert.js
+++ b/lib/assert.js
@@ -59,7 +59,7 @@ const {
   isRegExp,
 } = require('internal/util/types');
 const { isError, setOwnProperty } = require('internal/util');
-const { innerOk } = require('internal/assert/utils');
+const { innerOk, innerFail } = require('internal/assert/utils');
 
 const {
   validateFunction,
@@ -143,12 +143,6 @@ function Assert(options) {
 // they lose their `this` context and will use default behavior instead of the
 // instance's custom options.
 
-function innerFail(obj) {
-  if (obj.message instanceof Error) throw obj.message;
-
-  throw new AssertionError(obj);
-}
-
 /**
  * Throws an AssertionError with the given message.
  * @param {any | Error} [message]
@@ -189,7 +183,7 @@ assert.AssertionError = AssertionError;
  * @returns {void}
  */
 function assert(...args) {
-  innerOk(assert, args.length, ...args);
+  innerOk(assert, ...args);
 }
 
 /**
@@ -200,17 +194,17 @@ function assert(...args) {
  * @returns {void}
  */
 Assert.prototype.ok = function ok(...args) {
-  innerOk(ok, args.length, ...args);
+  innerOk(ok, ...args);
 };
 
 /**
  * The equality assertion tests shallow, coercive equality with ==.
  * @param {any} actual
  * @param {any} expected
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
-Assert.prototype.equal = function equal(actual, expected, message) {
+Assert.prototype.equal = function equal(actual, expected, ...message) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
@@ -232,10 +226,10 @@ Assert.prototype.equal = function equal(actual, expected, message) {
  * equal with !=.
  * @param {any} actual
  * @param {any} expected
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
-Assert.prototype.notEqual = function notEqual(actual, expected, message) {
+Assert.prototype.notEqual = function notEqual(actual, expected, ...message) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
@@ -256,10 +250,10 @@ Assert.prototype.notEqual = function notEqual(actual, expected, message) {
  * The deep equivalence assertion tests a deep equality relation.
  * @param {any} actual
  * @param {any} expected
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
-Assert.prototype.deepEqual = function deepEqual(actual, expected, message) {
+Assert.prototype.deepEqual = function deepEqual(actual, expected, ...message) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
@@ -280,10 +274,10 @@ Assert.prototype.deepEqual = function deepEqual(actual, expected, message) {
  * The deep non-equivalence assertion tests for any deep inequality.
  * @param {any} actual
  * @param {any} expected
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
-Assert.prototype.notDeepEqual = function notDeepEqual(actual, expected, message) {
+Assert.prototype.notDeepEqual = function notDeepEqual(actual, expected, ...message) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
@@ -305,10 +299,10 @@ Assert.prototype.notDeepEqual = function notDeepEqual(actual, expected, message)
  * relation.
  * @param {any} actual
  * @param {any} expected
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
-Assert.prototype.deepStrictEqual = function deepStrictEqual(actual, expected, message) {
+Assert.prototype.deepStrictEqual = function deepStrictEqual(actual, expected, ...message) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
@@ -330,11 +324,11 @@ Assert.prototype.deepStrictEqual = function deepStrictEqual(actual, expected, me
  * inequality.
  * @param {any} actual
  * @param {any} expected
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
 Assert.prototype.notDeepStrictEqual = notDeepStrictEqual;
-function notDeepStrictEqual(actual, expected, message) {
+function notDeepStrictEqual(actual, expected, ...message) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
@@ -355,10 +349,10 @@ function notDeepStrictEqual(actual, expected, message) {
  * The strict equivalence assertion tests a strict equality relation.
  * @param {any} actual
  * @param {any} expected
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
-Assert.prototype.strictEqual = function strictEqual(actual, expected, message) {
+Assert.prototype.strictEqual = function strictEqual(actual, expected, ...message) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
@@ -378,10 +372,10 @@ Assert.prototype.strictEqual = function strictEqual(actual, expected, message) {
  * The strict non-equivalence assertion tests for any strict inequality.
  * @param {any} actual
  * @param {any} expected
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
-Assert.prototype.notStrictEqual = function notStrictEqual(actual, expected, message) {
+Assert.prototype.notStrictEqual = function notStrictEqual(actual, expected, ...message) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
@@ -401,13 +395,13 @@ Assert.prototype.notStrictEqual = function notStrictEqual(actual, expected, mess
  * The strict equivalence assertion test between two objects
  * @param {any} actual
  * @param {any} expected
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
 Assert.prototype.partialDeepStrictEqual = function partialDeepStrictEqual(
   actual,
   expected,
-  message,
+  ...message
 ) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
@@ -464,7 +458,7 @@ function compareExceptionKey(actual, expected, key, message, keys, fn) {
     innerFail({
       actual,
       expected,
-      message,
+      message: [message],
       operator: fn.name,
       stackStartFn: fn,
       diff: this?.[kOptions]?.diff,
@@ -666,7 +660,7 @@ function expectsError(stackStartFn, actual, error, message) {
       actual: undefined,
       expected: error,
       operator: stackStartFn.name,
-      message: `Missing expected ${fnType}${details}`,
+      message: [`Missing expected ${fnType}${details}`],
       stackStartFn,
       diff: this?.[kOptions]?.diff,
     });
@@ -715,8 +709,8 @@ function expectsNoError(stackStartFn, actual, error, message) {
       actual,
       expected: error,
       operator: stackStartFn.name,
-      message: `Got unwanted ${fnType}${details}\n` +
-               `Actual message: "${actual?.message}"`,
+      message: [`Got unwanted ${fnType}${details}\n` +
+               `Actual message: "${actual?.message}"`],
       stackStartFn,
       diff: this?.[kOptions]?.diff,
     });
@@ -834,30 +828,26 @@ function internalMatch(string, regexp, message, fn) {
   const match = fn === Assert.prototype.match;
   if (typeof string !== 'string' ||
       RegExpPrototypeExec(regexp, string) !== null !== match) {
-    if (message instanceof Error) {
-      throw message;
-    }
 
-    const generatedMessage = !message;
+    const generatedMessage = message.length === 0;
 
     // 'The input was expected to not match the regular expression ' +
-    message ||= (typeof string !== 'string' ?
+    message[0] ||= (typeof string !== 'string' ?
       'The "string" argument must be of type string. Received type ' +
         `${typeof string} (${inspect(string)})` :
       (match ?
         'The input did not match the regular expression ' :
         'The input was expected to not match the regular expression ') +
           `${inspect(regexp)}. Input:\n\n${inspect(string)}\n`);
-    const err = new AssertionError({
+    innerFail({
       actual: string,
       expected: regexp,
       message,
       operator: fn.name,
       stackStartFn: fn,
       diff: this?.[kOptions]?.diff,
+      generatedMessage: generatedMessage,
     });
-    err.generatedMessage = generatedMessage;
-    throw err;
   }
 }
 
@@ -865,10 +855,10 @@ function internalMatch(string, regexp, message, fn) {
  * Expects the `string` input to match the regular expression.
  * @param {string} string
  * @param {RegExp} regexp
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
-Assert.prototype.match = function match(string, regexp, message) {
+Assert.prototype.match = function match(string, regexp, ...message) {
   internalMatch(string, regexp, message, match);
 };
 
@@ -876,10 +866,10 @@ Assert.prototype.match = function match(string, regexp, message) {
  * Expects the `string` input not to match the regular expression.
  * @param {string} string
  * @param {RegExp} regexp
- * @param {string | Error} [message]
+ * @param {string | Error | MessageFactory} [message]
  * @returns {void}
  */
-Assert.prototype.doesNotMatch = function doesNotMatch(string, regexp, message) {
+Assert.prototype.doesNotMatch = function doesNotMatch(string, regexp, ...message) {
   internalMatch(string, regexp, message, doesNotMatch);
 };
 
@@ -889,7 +879,7 @@ Assert.prototype.doesNotMatch = function doesNotMatch(string, regexp, message) {
  * @returns {void}
  */
 function strict(...args) {
-  innerOk(strict, args.length, ...args);
+  innerOk(strict, ...args);
 }
 
 ArrayPrototypeForEach([
diff --git a/lib/internal/assert/utils.js b/lib/internal/assert/utils.js
index cf7e45fe37..012f3e74da 100644
--- a/lib/internal/assert/utils.js
+++ b/lib/internal/assert/utils.js
@@ -3,15 +3,21 @@
 const {
   Error,
   ErrorCaptureStackTrace,
+  ErrorPrototypeToString,
   StringPrototypeCharCodeAt,
   StringPrototypeReplace,
 } = primordials;
 
 const {
+  codes: {
+    ERR_AMBIGUOUS_ARGUMENT,
+    ERR_INVALID_ARG_TYPE,
+  },
   isErrorStackTraceLimitWritable,
 } = require('internal/errors');
 const AssertionError = require('internal/assert/assertion_error');
 const { isError } = require('internal/util');
+const { format } = require('internal/util/inspect');
 
 const {
   getErrorSourceExpression,
@@ -33,6 +39,43 @@ const meta = [
 
 const escapeFn = (str) => meta[StringPrototypeCharCodeAt(str, 0)];
 
+/**
+ * A function that derives the failure message from the actual and expected values.
+ * It is invoked only when the assertion fails.
+ *
+ * Other return values than a string are ignored.
+ * @callback MessageFactory
+ * @param {any} actual
+ * @param {any} expected
+ * @returns {string}
+ */
+
+/**
+ * Raw message input is always passed internally as a tuple array.
+ * Accepted shapes:
+ *  - []
+ *  - [string]
+ *  - [string, ...any[]] (printf-like substitutions)
+ *  - [Error]
+ *  - [MessageFactory]
+ *
+ * Additional elements after [Error] or [MessageFactory] are rejected with ERR_AMBIGUOUS_ARGUMENT.
+ * A first element that is neither string, Error nor function is rejected with ERR_INVALID_ARG_TYPE.
+ * @typedef {[] | [string] | [string, ...any[]] | [Error] | [MessageFactory]} MessageTuple
+ */
+
+/**
+ * Options consumed by innerFail to construct and throw the AssertionError.
+ * @typedef {object} InnerFailOptions
+ * @property {any} actual Actual value
+ * @property {any} expected Expected value
+ * @property {MessageTuple} message Message
+ * @property {string} operator Operator
+ * @property {Function} stackStartFn Stack start function
+ * @property {'simple' | 'full'} [diff] Diff mode
+ * @property {boolean} [generatedMessage] Generated message
+ */
+
 function getErrMessage(fn) {
   const tmpLimit = Error.stackTraceLimit;
   const errorStackTraceLimitIsWritable = isErrorStackTraceLimitWritable();
@@ -52,32 +95,89 @@ function getErrMessage(fn) {
   }
 }
 
-function innerOk(fn, argLen, value, message) {
-  if (!value) {
-    let generatedMessage = false;
+/**
+ * @param {InnerFailOptions} obj
+ */
+function innerFail(obj) {
+  if (obj.message.length === 0) {
+    obj.message = undefined;
+  } else if (typeof obj.message[0] === 'string') {
+    if (obj.message.length > 1) {
+      obj.message = format(...obj.message);
+    } else {
+      obj.message = obj.message[0];
+    }
+  } else if (isError(obj.message[0])) {
+    if (obj.message.length > 1) {
+      throw new ERR_AMBIGUOUS_ARGUMENT(
+        'message',
+        `The error message was passed as error object "${ErrorPrototypeToString(obj.message[0])}" has trailing arguments that would be ignored.`,
+      );
+    }
+    throw obj.message[0];
+  } else if (typeof obj.message[0] === 'function') {
+    if (obj.message.length > 1) {
+      throw new ERR_AMBIGUOUS_ARGUMENT(
+        'message',
+        `The error message with function "${obj.message[0].name || 'anonymous'}" has trailing arguments that would be ignored.`,
+      );
+    }
+    try {
+      obj.message = obj.message[0](obj.actual, obj.expected);
+      if (typeof obj.message !== 'string') {
+        obj.message = undefined;
+      }
+    } catch {
+      // Ignore and use default message instead
+      obj.message = undefined;
+    }
+  } else {
+    throw new ERR_INVALID_ARG_TYPE(
+      'message',
+      ['string', 'function'],
+      obj.message[0],
+    );
+  }
 
-    if (argLen === 0) {
+  const error = new AssertionError(obj);
+  if (obj.generatedMessage !== undefined) {
+    error.generatedMessage = obj.generatedMessage;
+  }
+  throw error;
+}
+
+/**
+ * Internal ok handler delegating to innerFail for message handling.
+ * @param {Function} fn
+ * @param {...any} args
+ */
+function innerOk(fn, ...args) {
+  if (!args[0]) {
+    let generatedMessage = false;
+    let messageArgs;
+
+    if (args.length === 0) {
       generatedMessage = true;
-      message = 'No value argument passed to `assert.ok()`';
-    } else if (message == null) {
+      messageArgs = ['No value argument passed to `assert.ok()`'];
+    } else if (args.length === 1 || args[1] == null) {
       generatedMessage = true;
-      message = getErrMessage(fn);
-    } else if (isError(message)) {
-      throw message;
+      messageArgs = [getErrMessage(fn)];
+    } else {
+      messageArgs = args.slice(1);
     }
 
-    const err = new AssertionError({
-      actual: value,
+    innerFail({
+      actual: args[0],
       expected: true,
-      message,
+      message: messageArgs,
       operator: '==',
       stackStartFn: fn,
+      generatedMessage,
     });
-    err.generatedMessage = generatedMessage;
-    throw err;
   }
 }
 
 module.exports = {
   innerOk,
+  innerFail,
 };
diff --git a/lib/internal/test_runner/test.js b/lib/internal/test_runner/test.js
index 034840f221..fcde7e399c 100644
--- a/lib/internal/test_runner/test.js
+++ b/lib/internal/test_runner/test.js
@@ -333,7 +333,7 @@ class TestContext {
           if (plan !== null) {
             plan.count();
           }
-          innerOk(ok, args.length, ...args);
+          innerOk(ok, ...args);
         }
 
         assert.ok = ok;
diff --git a/test/fixtures/errors/error_exit.snapshot b/test/fixtures/errors/error_exit.snapshot
index 9594e08b4d..6cfb13f84f 100644
--- a/test/fixtures/errors/error_exit.snapshot
+++ b/test/fixtures/errors/error_exit.snapshot
@@ -1,6 +1,6 @@
 Exiting with code=1
-node:assert:*
-  throw new AssertionError(obj);
+node:internal*assert*utils:*
+  throw error;
   ^
 
 AssertionError [ERR_ASSERTION]: Expected values to be strictly equal:
diff --git a/test/parallel/test-assert.js b/test/parallel/test-assert.js
index ee48c0e1e2..e7e80b830b 100644
--- a/test/parallel/test-assert.js
+++ b/test/parallel/test-assert.js
@@ -904,10 +904,9 @@ test('Additional asserts', () => {
   assert.throws(
     () => assert(false, Symbol('foo')),
     {
-      code: 'ERR_ASSERTION',
-      constructor: assert.AssertionError,
-      generatedMessage: false,
-      message: 'Symbol(foo)'
+      code: 'ERR_INVALID_ARG_TYPE',
+      constructor: TypeError,
+      message: /"message" argument.+Symbol\(foo\)/
     }
   );
 
@@ -1595,5 +1594,188 @@ test('assert/strict exists', () => {
   assert.strictEqual(require('assert/strict'), assert.strict);
 });
 
+test('Printf-like format strings as error message', () => {
+  assert.throws(
+    () => assert.equal(1, 2, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.strictEqual(1, 2, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.notEqual(1, 1, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.notStrictEqual(1, 1, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.deepEqual(1, 2, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.notDeepEqual(1, 1, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.deepStrictEqual(1, 2, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.notDeepStrictEqual(1, 1, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.partialDeepStrictEqual(1, 2, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.match('foo', /bar/, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+
+  assert.throws(
+    () => assert.doesNotMatch('foo', /foo/, 'The answer to all questions is %i', 42),
+    /The answer to all questions is 42/
+  );
+});
+
+test('Functions as error message', () => {
+  function errorMessage(actual, expected) {
+    return `Nice message including ${actual} and ${expected}`;
+  }
+  assert.throws(
+    () => assert.equal(1, 2, errorMessage),
+    { message: 'Nice message including 1 and 2' }
+  );
+
+  assert.throws(
+    () => assert.strictEqual(1, 2, errorMessage),
+    // TODO(BridgeAR): Align input arguments with generated message for all
+    // methods.
+    // TODO(BridgeAR): Check how to handle this for custom messages. Do
+    // we need this? Should it be skipped for methods like these?
+    { message: 'Nice message including 1 and 2\n\n1 !== 2\n' }
+  );
+
+  assert.throws(
+    () => assert.notEqual(1, 1, errorMessage),
+    { message: 'Nice message including 1 and 1' }
+  );
+
+  assert.throws(
+    () => assert.notStrictEqual(1, 1, errorMessage),
+    { message: 'Nice message including 1 and 1' }
+  );
+
+  assert.throws(
+    () => assert.deepEqual(1, 2, errorMessage),
+    { message: 'Nice message including 1 and 2' }
+  );
+
+  assert.throws(
+    () => assert.notDeepEqual(1, 1, errorMessage),
+    { message: 'Nice message including 1 and 1' }
+  );
+
+  assert.throws(
+    () => assert.deepStrictEqual(1, 2, errorMessage),
+    { message: 'Nice message including 1 and 2\n\n1 !== 2\n' }
+  );
+
+  assert.throws(
+    () => assert.notDeepStrictEqual(1, 1, errorMessage),
+    { message: 'Nice message including 1 and 1' }
+  );
+
+  assert.throws(
+    () => assert.partialDeepStrictEqual(1, 2, errorMessage),
+    { message: 'Nice message including 1 and 2\n\n1 !== 2\n' }
+  );
+
+  assert.throws(
+    () => assert.match('foo', /bar/, errorMessage),
+    { message: 'Nice message including foo and /bar/' }
+  );
+
+  assert.throws(
+    () => assert.doesNotMatch('foo', /foo/, errorMessage),
+    { message: 'Nice message including foo and /foo/' }
+  );
+});
+
+test('Ambiguous error messages fail', () => {
+  function errorMessage(actual, expected) {
+    return `Nice message including ${actual} and ${expected}`;
+  }
+
+  assert.throws(
+    () => assert.doesNotMatch('foo', /foo/, errorMessage, 'foobar'),
+    {
+      code: 'ERR_AMBIGUOUS_ARGUMENT',
+      message: /errorMessage/
+    }
+  );
+
+  assert.throws(
+    () => assert.doesNotMatch('foo', /foo/, new Error('baz'), 'foobar'),
+    {
+      code: 'ERR_AMBIGUOUS_ARGUMENT',
+      message: /baz/
+    }
+  );
+});
+
+test('Faulty message functions', () => {
+  assert.throws(
+    () => assert.doesNotMatch('foo', /foo/, (a, b) => 123),
+    {
+      code: 'ERR_ASSERTION',
+      message: "'foo' doesNotMatch /foo/"
+    }
+  );
+
+  assert.throws(
+    () => assert.match('foo', /123/, (a, b) => { new Error('baz'); }),
+    {
+      code: 'ERR_ASSERTION',
+      message: "'foo' match /123/"
+    }
+  );
+});
+
+test('Functions as error message', () => {
+  function errorMessage(actual, expected) {
+    return `Nice message including ${actual} and ${expected}`;
+  }
+
+  assert.throws(
+    () => assert.equal('foo', 'bar', errorMessage),
+    {
+      code: 'ERR_ASSERTION',
+      message: /Nice message including foo and bar/
+    }
+  );
+
+  assert.throws(
+    () => assert.doesNotMatch('foo', /foo/, errorMessage),
+    {
+      code: 'ERR_ASSERTION',
+      message: /Nice message including foo and \/foo\//
+    }
+  );
+});
+
 /* eslint-enable no-restricted-syntax */
 /* eslint-enable no-restricted-properties */