diff --git a/Sources/Nimble/Matchers/Map.swift b/Sources/Nimble/Matchers/Map.swift
index 7132ab3c4..509a49799 100644
--- a/Sources/Nimble/Matchers/Map.swift
+++ b/Sources/Nimble/Matchers/Map.swift
@@ -1,7 +1,7 @@
 /// `map` works by transforming the expression to a value that the given matcher uses.
 ///
 /// For example, you might only care that a particular property on a method equals some other value.
-/// So, you could write `expect(myObject).to(lens(\.someIntValue, equal(3))`.
+/// So, you could write `expect(myObject).to(map(\.someIntValue, equal(3))`.
 /// This is also useful in conjunction with ``satisfyAllOf`` to do a partial equality of an object.
 public func map<T, U>(_ transform: @escaping (T) throws -> U, _ matcher: Matcher<U>) -> Matcher<T> {
     Matcher { (received: Expression<T>) in
@@ -15,7 +15,7 @@ public func map<T, U>(_ transform: @escaping (T) throws -> U, _ matcher: Matcher
 /// `map` works by transforming the expression to a value that the given matcher uses.
 ///
 /// For example, you might only care that a particular property on a method equals some other value.
-/// So, you could write `expect(myObject).to(lens(\.someIntValue, equal(3))`.
+/// So, you could write `expect(myObject).to(map(\.someIntValue, equal(3))`.
 /// This is also useful in conjunction with ``satisfyAllOf`` to do a partial equality of an object.
 public func map<T, U>(_ transform: @escaping (T) async throws -> U, _ matcher: some AsyncableMatcher<U>) -> AsyncMatcher<T> {
     AsyncMatcher { (received: AsyncExpression<T>) in
@@ -25,3 +25,45 @@ public func map<T, U>(_ transform: @escaping (T) async throws -> U, _ matcher: s
         })
     }
 }
+
+/// `map` works by transforming the expression to a value that the given matcher uses.
+///
+/// For example, you might only care that a particular property on a method equals some other value.
+/// So, you could write `expect(myObject).to(compactMap({ $0 as? Int }, equal(3))`.
+/// This is also useful in conjunction with ``satisfyAllOf`` to match against a converted type.
+public func map<T, U>(_ transform: @escaping (T) throws -> U?, _ matcher: Matcher<U>) -> Matcher<T> {
+    Matcher { (received: Expression<T>) in
+        let message = ExpectationMessage.expectedTo("Map from \(T.self) to \(U.self)")
+
+        guard let value = try received.evaluate() else {
+            return MatcherResult(status: .fail, message: message.appendedBeNilHint())
+        }
+
+        guard let transformedValue = try transform(value) else {
+            return MatcherResult(status: .fail, message: message)
+        }
+
+        return try matcher.satisfies(Expression(expression: { transformedValue }, location: received.location))
+    }
+}
+
+/// `map` works by transforming the expression to a value that the given matcher uses.
+///
+/// For example, you might only care that a particular property on a method equals some other value.
+/// So, you could write `expect(myObject).to(compactMap({ $0 as? Int }, equal(3))`.
+/// This is also useful in conjunction with ``satisfyAllOf`` to match against a converted type.
+public func map<T, U>(_ transform: @escaping (T) async throws -> U?, _ matcher: some AsyncableMatcher<U>) -> AsyncMatcher<T> {
+    AsyncMatcher { (received: AsyncExpression<T>) in
+        let message = ExpectationMessage.expectedTo("Map from \(T.self) to \(U.self)")
+
+        guard let value = try await received.evaluate() else {
+            return MatcherResult(status: .fail, message: message.appendedBeNilHint())
+        }
+
+        guard let transformedValue = try await transform(value) else {
+            return MatcherResult(status: .fail, message: message)
+        }
+
+        return try await matcher.satisfies(AsyncExpression(expression: { transformedValue }, location: received.location))
+    }
+}
diff --git a/Tests/NimbleTests/Matchers/MapTest.swift b/Tests/NimbleTests/Matchers/MapTest.swift
index 9b13c5f64..cc361f4df 100644
--- a/Tests/NimbleTests/Matchers/MapTest.swift
+++ b/Tests/NimbleTests/Matchers/MapTest.swift
@@ -5,6 +5,7 @@ import NimbleSharedTestHelpers
 #endif
 
 final class MapTest: XCTestCase {
+    // MARK: Map
     func testMap() {
         expect(1).to(map({ $0 }, equal(1)))
 
@@ -80,4 +81,81 @@ final class MapTest: XCTestCase {
             map(\.string, equal("world"))
         ))
     }
+
+    // MARK: Failable map
+    func testFailableMap() {
+        expect("1").to(map({ Int($0) }, equal(1)))
+
+        struct Value {
+            let int: Int?
+            let string: String?
+        }
+
+        expect(Value(
+            int: 1,
+            string: "hello"
+        )).to(satisfyAllOf(
+            map(\.int, equal(1)),
+            map(\.string, equal("hello"))
+        ))
+
+        expect(Value(
+            int: 1,
+            string: "hello"
+        )).to(satisfyAnyOf(
+            map(\.int, equal(2)),
+            map(\.string, equal("hello"))
+        ))
+
+        expect(Value(
+            int: 1,
+            string: "hello"
+        )).toNot(satisfyAllOf(
+            map(\.int, equal(2)),
+            map(\.string, equal("hello"))
+        ))
+    }
+
+    func testFailableMapAsync() async {
+        struct Value {
+            let int: Int?
+            let string: String?
+        }
+
+        await expect(Value(
+            int: 1,
+            string: "hello"
+        )).to(map(\.int, asyncEqual(1)))
+
+        await expect(Value(
+            int: 1,
+            string: "hello"
+        )).toNot(map(\.int, asyncEqual(2)))
+    }
+
+    func testFailableMapWithAsyncFunction() async {
+        func someOperation(_ value: Int) async -> String? {
+            "\(value)"
+        }
+        await expect(1).to(map(someOperation, equal("1")))
+    }
+
+    func testFailableMapWithActor() {
+        actor Box {
+            let int: Int?
+            let string: String?
+
+            init(int: Int, string: String) {
+                self.int = int
+                self.string = string
+            }
+        }
+
+        let box = Box(int: 3, string: "world")
+
+        expect(box).to(satisfyAllOf(
+            map(\.int, equal(3)),
+            map(\.string, equal("world"))
+        ))
+    }
 }