diff --git a/docs/03-assertions.md b/docs/03-assertions.md
index ad7725f99..6714a84a9 100644
--- a/docs/03-assertions.md
+++ b/docs/03-assertions.md
@@ -172,7 +172,10 @@ Assert that an error is thrown. `fn` must be a function which should throw. The
 
 * `instanceOf`: a constructor, the thrown error must be an instance of
 * `is`: the thrown error must be strictly equal to `expectation.is`
-* `message`: either a string, which is compared against the thrown error's message, or a regular expression, which is matched against this message
+* `message`: the following types are valid: 
+  * *string* - it is compared against the thrown error's message
+  * *regular expression* - it is matched against this message
+  * *function* - it is passed the thrown error message and must return a boolean for whether the assertion passed
 * `name`: the expected `.name` value of the thrown error
 * `code`: the expected `.code` value of the thrown error
 
@@ -204,7 +207,10 @@ The thrown value *must* be an error. It is returned so you can run more assertio
 
 * `instanceOf`: a constructor, the thrown error must be an instance of
 * `is`: the thrown error must be strictly equal to `expectation.is`
-* `message`: either a string, which is compared against the thrown error's message, or a regular expression, which is matched against this message
+* `message`: the following types are valid: 
+  * *string* - it is compared against the thrown error's message
+  * *regular expression* - it is matched against this message
+  * *function* - it is passed the thrown error message and must return a boolean for whether the assertion passed
 * `name`: the expected `.name` value of the thrown error
 * `code`: the expected `.code` value of the thrown error
 
diff --git a/lib/assert.js b/lib/assert.js
index 70d24d1bf..5d5477071 100644
--- a/lib/assert.js
+++ b/lib/assert.js
@@ -106,10 +106,15 @@ function validateExpectations(assertion, expectations, numberArgs) { // eslint-d
 			});
 		}
 
-		if (hasOwnProperty(expectations, 'message') && typeof expectations.message !== 'string' && !(expectations.message instanceof RegExp)) {
+		if (
+			hasOwnProperty(expectations, 'message')
+			&& typeof expectations.message !== 'string'
+			&& !(expectations.message instanceof RegExp)
+			&& !(typeof expectations.message === 'function')
+		) {
 			throw new AssertionError({
 				assertion,
-				message: `The \`message\` property of the second argument to \`t.${assertion}()\` must be a string or regular expression`,
+				message: `The \`message\` property of the second argument to \`t.${assertion}()\` must be a string, regular expression or a function`,
 				values: [formatWithLabel('Called with:', expectations)],
 			});
 		}
@@ -230,6 +235,19 @@ function assertExpectations({assertion, actual, expectations, message, prefix, s
 		});
 	}
 
+	if (typeof expectations.message === 'function' && expectations.message(actual.message) === false) {
+		throw new AssertionError({
+			assertion,
+			message,
+			savedError,
+			actualStack,
+			values: [
+				formatWithLabel(`${prefix} unexpected exception:`, actual),
+				formatWithLabel('Expected message to return true:', expectations.message),
+			],
+		});
+	}
+
 	if (typeof expectations.code !== 'undefined' && actual.code !== expectations.code) {
 		throw new AssertionError({
 			assertion,
diff --git a/test-tap/assert.js b/test-tap/assert.js
index c21bbc7d9..d4c0b369c 100644
--- a/test-tap/assert.js
+++ b/test-tap/assert.js
@@ -899,6 +899,78 @@ test('.throws()', gather(t => {
 			formatted: /null/,
 		}],
 	});
+
+	// Fails because the string in the message is incorrect
+	failsWith(
+		t,
+		() =>
+			assertions.throws(
+				() => {
+					throw new Error('error');
+				},
+				{message: 'my error'},
+			),
+		{
+			assertion: 'throws',
+			message: '',
+			values: [
+				{label: 'Function threw unexpected exception:', formatted: /error/},
+				{label: 'Expected message to equal:', formatted: /my error/},
+			],
+		},
+	);
+
+	passes(t, () => assertions.throws(() => {
+		throw new Error('error');
+	}, {message: 'error'}));
+
+	// Fails because the regular expression in the message is incorrect
+	failsWith(
+		t,
+		() =>
+			assertions.throws(
+				() => {
+					throw new Error('error');
+				},
+				{message: /my error/},
+			),
+		{
+			assertion: 'throws',
+			message: '',
+			values: [
+				{label: 'Function threw unexpected exception:', formatted: /error/},
+				{label: 'Expected message to match:', formatted: /my error/},
+			],
+		},
+	);
+
+	passes(t, () => assertions.throws(() => {
+		throw new Error('error');
+	}, {message: /error/}));
+
+	// Fails because the function in the message returns false
+	failsWith(
+		t,
+		() =>
+			assertions.throws(
+				() => {
+					throw new Error('error');
+				},
+				{message: () => false},
+			),
+		{
+			assertion: 'throws',
+			message: '',
+			values: [
+				{label: 'Function threw unexpected exception:', formatted: /error/},
+				{label: 'Expected message to return true:', formatted: /Function/},
+			],
+		},
+	);
+
+	passes(t, () => assertions.throws(() => {
+		throw new Error('error');
+	}, {message: () => true}));
 }));
 
 test('.throws() returns the thrown error', t => {
@@ -1066,7 +1138,7 @@ test('.throws() fails if passed a bad expectation', t => {
 
 	failsWith(t, () => assertions.throws(() => {}, {message: null}), {
 		assertion: 'throws',
-		message: 'The `message` property of the second argument to `t.throws()` must be a string or regular expression',
+		message: 'The `message` property of the second argument to `t.throws()` must be a string, regular expression or a function',
 		values: [{label: 'Called with:', formatted: /message: null/}],
 	});
 
@@ -1136,7 +1208,7 @@ test('.throwsAsync() fails if passed a bad expectation', t => {
 
 	failsWith(t, () => assertions.throwsAsync(() => {}, {message: null}), {
 		assertion: 'throwsAsync',
-		message: 'The `message` property of the second argument to `t.throwsAsync()` must be a string or regular expression',
+		message: 'The `message` property of the second argument to `t.throwsAsync()` must be a string, regular expression or a function',
 		values: [{label: 'Called with:', formatted: /message: null/}],
 	}, {expectBoolean: false});
 
diff --git a/types/assertions.d.ts b/types/assertions.d.ts
index ce5a97a14..0d2c8506b 100644
--- a/types/assertions.d.ts
+++ b/types/assertions.d.ts
@@ -12,7 +12,7 @@ export type ThrowsExpectation = {
 	is?: Error;
 
 	/** The thrown error must have a message that equals the given string, or matches the regular expression. */
-	message?: string | RegExp;
+	message?: string | RegExp | ((message: string) => boolean);
 
 	/** The thrown error must have a name that equals the given string. */
 	name?: string;