diff --git a/Sources/Testing/Issues/KnownIssue.swift b/Sources/Testing/Issues/KnownIssue.swift
index f59185388..17214c12c 100644
--- a/Sources/Testing/Issues/KnownIssue.swift
+++ b/Sources/Testing/Issues/KnownIssue.swift
@@ -77,6 +77,13 @@ struct KnownIssueScope: Sendable {
 ///   - sourceLocation: The source location to which the issue should be
 ///     attributed.
 private func _matchError(_ error: any Error, in scope: KnownIssueScope, comment: Comment?, sourceLocation: SourceLocation) throws {
+  // ExpectationFailedError is thrown by expectation checking functions to
+  // indicate a condition evaluated to `false`. Those functions record their
+  // own issue, so we don't need to create a new issue and attempt to match it.
+  if error is ExpectationFailedError {
+    return
+  }
+
   let sourceContext = SourceContext(backtrace: Backtrace(forFirstThrowOf: error), sourceLocation: sourceLocation)
   var issue = Issue(kind: .errorCaught(error), comments: [], sourceContext: sourceContext)
   if let context = scope.matcher(issue) {
diff --git a/Tests/TestingTests/KnownIssueTests.swift b/Tests/TestingTests/KnownIssueTests.swift
index 9174bfdd8..88deef5ec 100644
--- a/Tests/TestingTests/KnownIssueTests.swift
+++ b/Tests/TestingTests/KnownIssueTests.swift
@@ -574,6 +574,26 @@ final class KnownIssueTests: XCTestCase {
     await fulfillment(of: [issueRecorded, knownIssueNotRecorded], timeout: 0.0)
   }
 
+  func testKnownIssueWithRequiredExpectationFailure() async {
+    let issueRecorded = expectation(description: "Issue recorded")
+
+    var configuration = Configuration()
+    configuration.eventHandler = { event, _ in
+      guard case .issueRecorded = event.kind else {
+        return
+      }
+      issueRecorded.fulfill()
+    }
+
+    await Test {
+      withKnownIssue {
+        try #require(Bool(false))
+      }
+    }.run(configuration: configuration)
+
+    await fulfillment(of: [issueRecorded], timeout: 0.0)
+  }
+
   func testAsyncKnownIssueThatDoesNotAlwaysOccur() async {
     struct MyError: Error {}