diff --git a/Sources/TestingMacros/Support/ConditionArgumentParsing.swift b/Sources/TestingMacros/Support/ConditionArgumentParsing.swift
index d59d7600d..30f0cd430 100644
--- a/Sources/TestingMacros/Support/ConditionArgumentParsing.swift
+++ b/Sources/TestingMacros/Support/ConditionArgumentParsing.swift
@@ -312,17 +312,6 @@ private func _exprFromOptionalChainedExpr(_ expr: some ExprSyntaxProtocol) -> (E
 ///
 /// - Returns: An instance of ``Condition`` describing `expr`.
 private func _parseCondition(from expr: FunctionCallExprSyntax, for macro: some FreestandingMacroExpansionSyntax, in context: some MacroExpansionContext) -> Condition {
-  // If the member function call involves the `try` or `await` keywords, assume
-  // we cannot expand it. This check cannot handle expressions like
-  // `try #expect(a.b(c))` where `b()` is throwing because the `try` keyword
-  // is outside the macro expansion. SEE: rdar://109470248
-  let containsTryOrAwait = expr.tokens(viewMode: .sourceAccurate).lazy
-    .map(\.tokenKind)
-    .contains { $0 == .keyword(.try) || $0 == .keyword(.await) }
-  if containsTryOrAwait {
-    return Condition(expression: expr)
-  }
-
   // We do not support function calls with trailing closures because the
   // transform required to forward them requires more information than is
   // available solely from the syntax tree.
@@ -477,6 +466,22 @@ private func _parseCondition(negating expr: ExprSyntax, isParenthetical: Bool, f
 ///
 /// - Returns: An instance of ``Condition`` describing `expr`.
 private func _parseCondition(from expr: ExprSyntax, for macro: some FreestandingMacroExpansionSyntax, in context: some MacroExpansionContext) -> Condition {
+  // Handle closures with a single expression in them (e.g. { $0.foo() })
+  if let closureExpr = expr.as(ClosureExprSyntax.self) {
+    return _parseCondition(from: closureExpr, for: macro, in: context)
+  }
+
+  // If the condition involves the `try` or `await` keywords, assume we cannot
+  // expand it. This check cannot handle expressions like
+  // `try #expect(a.b(c))` where `b()` is throwing because the `try` keyword is
+  // outside the macro expansion. SEE: rdar://109470248
+  let containsTryOrAwait = expr.tokens(viewMode: .sourceAccurate).lazy
+    .map(\.tokenKind)
+    .contains { $0 == .keyword(.try) || $0 == .keyword(.await) }
+  if containsTryOrAwait {
+    return Condition(expression: expr)
+  }
+
   if let infixOperator = expr.as(InfixOperatorExprSyntax.self),
      let op = infixOperator.operator.as(BinaryOperatorExprSyntax.self) {
     return _parseCondition(from: expr, leftOperand: infixOperator.leftOperand, operator: op, rightOperand: infixOperator.rightOperand, for: macro, in: context)
@@ -489,11 +494,6 @@ private func _parseCondition(from expr: ExprSyntax, for macro: some Freestanding
     return _parseCondition(from: asExpr, for: macro, in: context)
   }
 
-  // Handle closures with a single expression in them (e.g. { $0.foo() })
-  if let closureExpr = expr.as(ClosureExprSyntax.self) {
-    return _parseCondition(from: closureExpr, for: macro, in: context)
-  }
-
   // Handle function calls and member accesses.
   if let functionCallExpr = expr.as(FunctionCallExprSyntax.self) {
     return _parseCondition(from: functionCallExpr, for: macro, in: context)
diff --git a/Tests/TestingTests/MiscellaneousTests.swift b/Tests/TestingTests/MiscellaneousTests.swift
index 33980cf38..32a86df6b 100644
--- a/Tests/TestingTests/MiscellaneousTests.swift
+++ b/Tests/TestingTests/MiscellaneousTests.swift
@@ -123,6 +123,15 @@ struct SendableTests: Sendable {
 
   @Test(.hidden, arguments: FixtureData.stringReturningClosureArray)
   func parameterizedAcceptingFunction(f: @Sendable () -> String) {}
+
+  @Test(.hidden) func throwKeywordInExpectation() throws {
+    #expect(UInt() == UInt(try #require(Int("0"))))
+  }
+
+  @Test(.hidden) func asyncKeywordInExpectation() async {
+    func f() async -> Int { 0 }
+    #expect(UInt() == UInt(await f()))
+  }
 }
 
 @Suite("Named Sendable test type", .hidden)