diff --git a/Sources/IssueReporting/ErrorReporting.swift b/Sources/IssueReporting/ErrorReporting.swift
index f83df31..a48974c 100644
--- a/Sources/IssueReporting/ErrorReporting.swift
+++ b/Sources/IssueReporting/ErrorReporting.swift
@@ -56,6 +56,38 @@ public func withErrorReporting<R>(
   }
 }
 
+/// Evaluates a throwing closure and automatically catches and reports any error thrown.
+///
+/// - Parameters:
+///   - message: A message describing the expectation.
+///   - reporters: Issue reporters to notify during the operation.
+///   - fileID: The source `#fileID` associated with the error reporting.
+///   - filePath: The source `#filePath` associated with the error reporting.
+///   - line: The source `#line` associated with the error reporting.
+///   - column: The source `#column` associated with the error reporting.
+///   - body: A synchronous operation.
+/// - Returns: The optional result of the operation, or `nil` if an error was thrown.
+@_transparent
+public func withErrorReporting<R>(
+  _ message: @autoclosure () -> String? = nil,
+  to reporters: [any IssueReporter]? = nil,
+  fileID: StaticString = #fileID,
+  filePath: StaticString = #filePath,
+  line: UInt = #line,
+  column: UInt = #column,
+  catching body: () throws -> R?
+) -> R? {
+  (withErrorReporting(
+    message(),
+    to: reporters,
+    fileID: fileID,
+    filePath: filePath,
+    line: line,
+    column: column,
+    catching: body
+  ) as R??) ?? nil
+}
+
 #if compiler(>=6)
   /// Evaluates a throwing closure and automatically catches and reports any error thrown.
   ///
@@ -113,6 +145,42 @@ public func withErrorReporting<R>(
       }
     }
   }
+
+  /// Evaluates a throwing closure and automatically catches and reports any error thrown.
+  ///
+  /// - Parameters:
+  ///   - message: A message describing the expectation.
+  ///   - reporters: Issue reporters to notify during the operation.
+  ///   - fileID: The source `#fileID` associated with the error reporting.
+  ///   - filePath: The source `#filePath` associated with the error reporting.
+  ///   - line: The source `#line` associated with the error reporting.
+  ///   - column: The source `#column` associated with the error reporting.
+  ///   - isolation: The isolation associated with the error reporting.
+  ///   - body: An asynchronous operation.
+  /// - Returns: The optional result of the operation, or `nil` if an error was thrown.
+  @_transparent
+  public func withErrorReporting<R>(
+    _ message: @autoclosure () -> String? = nil,
+    to reporters: [any IssueReporter]? = nil,
+    fileID: StaticString = #fileID,
+    filePath: StaticString = #filePath,
+    line: UInt = #line,
+    column: UInt = #column,
+    isolation: isolated (any Actor)? = #isolation,
+    // DO NOT FIX THE WHITESPACE IN THE NEXT LINE UNTIL 5.10 IS UNSUPPORTED
+    // https://github.com/swiftlang/swift/issues/79285
+    catching body: () async throws -> sending R?
+  ) async -> R? {
+    (await withErrorReporting(
+      message(),
+      to: reporters,
+      fileID: fileID,
+      filePath: filePath,
+      line: line,
+      column: column,
+      catching: body
+    ) as R??) ?? nil
+  }
 #else
   @_transparent
   @_unsafeInheritExecutor
@@ -157,4 +225,26 @@ public func withErrorReporting<R>(
       }
     }
   }
+
+  @_transparent
+  @_unsafeInheritExecutor
+  public func withErrorReporting<R>(
+    _ message: @autoclosure () -> String? = nil,
+    to reporters: [any IssueReporter]? = nil,
+    fileID: StaticString = #fileID,
+    filePath: StaticString = #filePath,
+    line: UInt = #line,
+    column: UInt = #column,
+    catching body: () async throws -> R?
+  ) async -> R? {
+    (await withErrorReporting(
+      message(),
+      to: reporters,
+      fileID: fileID,
+      filePath: filePath,
+      line: line,
+      column: column,
+      catching: body
+    ) as R??) ?? nil
+  }
 #endif
diff --git a/Tests/IssueReportingTests/WithErrorReportingTests.swift b/Tests/IssueReportingTests/WithErrorReportingTests.swift
index c54b533..445bb9d 100644
--- a/Tests/IssueReportingTests/WithErrorReportingTests.swift
+++ b/Tests/IssueReportingTests/WithErrorReportingTests.swift
@@ -40,6 +40,28 @@
       }
     }
 
+    @Test func squashOptionalSync() async {
+      withKnownIssue {
+        let _: Int? = withErrorReporting { () -> Int? in
+          throw SomeError()
+        }
+      } matching: { issue in
+        issue.description == "Caught error: SomeError()\(issueDescriptionSuffix)"
+      }
+    }
+
+
+    @Test func squashOptionalAsync() async {
+      await withKnownIssue {
+        let _: Int? = await withErrorReporting { () -> Int? in
+          await Task.yield()
+          throw SomeError()
+        }
+      } matching: { issue in
+        issue.description == "Caught error: SomeError()\(issueDescriptionSuffix)"
+      }
+    }
+
     #if compiler(<6.2)
       @MainActor
       @Test func isolation() async {