diff --git a/Sources/SwiftIfConfig/ConfiguredRegions.swift b/Sources/SwiftIfConfig/ConfiguredRegions.swift
index f562e770bd5..f4553e09a7b 100644
--- a/Sources/SwiftIfConfig/ConfiguredRegions.swift
+++ b/Sources/SwiftIfConfig/ConfiguredRegions.swift
@@ -65,7 +65,18 @@ fileprivate class ConfiguredRegionVisitor<Configuration: BuildConfiguration>: Sy
     // If we're in an active region, find the active clause. Otherwise,
     // there isn't one.
     let activeClause = inActiveRegion ? node.activeClause(in: configuration).clause : nil
+    var foundActive = false
+    var syntaxErrorsAllowed = false
     for clause in node.clauses {
+      // If we haven't found the active clause yet, syntax errors are allowed
+      // depending on this clause.
+      if !foundActive {
+        syntaxErrorsAllowed =
+          clause.condition.map {
+            IfConfigClauseSyntax.syntaxErrorsAllowed($0).syntaxErrorsAllowed
+          } ?? false
+      }
+
       // If this is the active clause, record it and then recurse into the
       // elements.
       if clause == activeClause {
@@ -77,14 +88,10 @@ fileprivate class ConfiguredRegionVisitor<Configuration: BuildConfiguration>: Sy
           walk(elements)
         }
 
+        foundActive = true
         continue
       }
 
-      // For inactive clauses, distinguish between inactive and unparsed.
-      let syntaxErrorsAllowed = clause.syntaxErrorsAllowed(
-        configuration: configuration
-      ).syntaxErrorsAllowed
-
       // If this is within an active region, or this is an unparsed region,
       // record it.
       if inActiveRegion || syntaxErrorsAllowed {
diff --git a/Sources/SwiftIfConfig/IfConfigDecl+IfConfig.swift b/Sources/SwiftIfConfig/IfConfigDecl+IfConfig.swift
index 68e9e6b7b48..d5d286d4ba7 100644
--- a/Sources/SwiftIfConfig/IfConfigDecl+IfConfig.swift
+++ b/Sources/SwiftIfConfig/IfConfigDecl+IfConfig.swift
@@ -43,9 +43,13 @@ extension IfConfigDeclSyntax {
         return (clause, diagnostics: diagnostics)
       }
 
+      // Apply operator folding for !/&&/||.
+      let (foldedCondition, foldingDiagnostics) = IfConfigClauseSyntax.foldOperators(condition)
+      diagnostics.append(contentsOf: foldingDiagnostics)
+
       // If this condition evaluates true, return this clause.
       let (isActive, _, localDiagnostics) = evaluateIfConfig(
-        condition: condition,
+        condition: foldedCondition,
         configuration: configuration
       )
       diagnostics.append(contentsOf: localDiagnostics)
diff --git a/Sources/SwiftIfConfig/IfConfigEvaluation.swift b/Sources/SwiftIfConfig/IfConfigEvaluation.swift
index ac4b95e350d..2ed3ccb4c37 100644
--- a/Sources/SwiftIfConfig/IfConfigEvaluation.swift
+++ b/Sources/SwiftIfConfig/IfConfigEvaluation.swift
@@ -11,6 +11,7 @@
 //===----------------------------------------------------------------------===//
 
 import SwiftDiagnostics
+import SwiftOperators
 import SwiftSyntax
 
 /// Evaluate the condition of an `#if`.
@@ -433,20 +434,77 @@ func evaluateIfConfig(
 }
 
 extension IfConfigClauseSyntax {
-  /// Determine whether this condition is "syntaxErrorsAllowed".
-  func syntaxErrorsAllowed(
-    configuration: some BuildConfiguration
+  /// Fold the operators within an #if condition, turning sequence expressions
+  /// involving the various allowed operators (&&, ||, !) into well-structured
+  /// binary operators.
+  public static func foldOperators(
+    _ condition: some ExprSyntaxProtocol
+  ) -> (folded: ExprSyntax, diagnostics: [Diagnostic]) {
+    var foldingDiagnostics: [Diagnostic] = []
+    let foldedCondition = OperatorTable.logicalOperators.foldAll(condition) { error in
+      foldingDiagnostics.append(contentsOf: error.asDiagnostics(at: condition))
+    }.cast(ExprSyntax.self)
+    return (folded: foldedCondition, diagnostics: foldingDiagnostics)
+  }
+
+  /// Determine whether the given expression, when used as the condition in
+  /// an inactive `#if` clause, implies that syntax errors are permitted within
+  /// that region.
+  public static func syntaxErrorsAllowed(
+    _ condition: some ExprSyntaxProtocol
   ) -> (syntaxErrorsAllowed: Bool, diagnostics: [Diagnostic]) {
-    guard let condition else {
-      return (syntaxErrorsAllowed: false, diagnostics: [])
-    }
+    let (foldedCondition, foldingDiagnostics) = IfConfigClauseSyntax.foldOperators(condition)
 
-    // Evaluate this condition against the build configuration.
-    let (_, syntaxErrorsAllowed, diagnostics) = evaluateIfConfig(
-      condition: condition,
-      configuration: configuration
+    return (
+      !foldingDiagnostics.isEmpty || foldedCondition.allowsSyntaxErrorsFolded,
+      foldingDiagnostics
     )
+  }
+}
+
+extension ExprSyntaxProtocol {
+  /// Determine whether this expression, when used as a condition within a #if
+  /// that evaluates false, implies that the code contained in that `#if`
+  ///
+  /// Check whether of allowsSyntaxErrors(_:) that assumes that inputs have
+  /// already been operator-folded.
+  var allowsSyntaxErrorsFolded: Bool {
+    // Logical '!'.
+    if let prefixOp = self.as(PrefixOperatorExprSyntax.self),
+      prefixOp.operator.text == "!"
+    {
+      return prefixOp.expression.allowsSyntaxErrorsFolded
+    }
+
+    // Logical '&&' and '||'.
+    if let binOp = self.as(InfixOperatorExprSyntax.self),
+      let op = binOp.operator.as(BinaryOperatorExprSyntax.self)
+    {
+      switch op.operator.text {
+      case "&&":
+        return binOp.leftOperand.allowsSyntaxErrorsFolded || binOp.rightOperand.allowsSyntaxErrorsFolded
+      case "||":
+        return binOp.leftOperand.allowsSyntaxErrorsFolded && binOp.rightOperand.allowsSyntaxErrorsFolded
+      default:
+        return false
+      }
+    }
+
+    // Look through parentheses.
+    if let tuple = self.as(TupleExprSyntax.self), tuple.isParentheses,
+      let element = tuple.elements.first
+    {
+      return element.expression.allowsSyntaxErrorsFolded
+    }
+
+    // Call syntax is for operations.
+    if let call = self.as(FunctionCallExprSyntax.self),
+      let fnName = call.calledExpression.simpleIdentifierExpr,
+      let fn = IfConfigFunctions(rawValue: fnName)
+    {
+      return fn.syntaxErrorsAllowed
+    }
 
-    return (syntaxErrorsAllowed, diagnostics)
+    return false
   }
 }
diff --git a/Sources/SwiftIfConfig/IfConfigRegionState.swift b/Sources/SwiftIfConfig/IfConfigRegionState.swift
index 50a1ab0369b..5d2553d1d4a 100644
--- a/Sources/SwiftIfConfig/IfConfigRegionState.swift
+++ b/Sources/SwiftIfConfig/IfConfigRegionState.swift
@@ -32,10 +32,7 @@ public enum IfConfigRegionState {
     in configuration: some BuildConfiguration
   ) -> (state: IfConfigRegionState, syntaxErrorsAllowed: Bool, diagnostics: [Diagnostic]) {
     // Apply operator folding for !/&&/||.
-    var foldingDiagnostics: [Diagnostic] = []
-    let foldedCondition = OperatorTable.logicalOperators.foldAll(condition) { error in
-      foldingDiagnostics.append(contentsOf: error.asDiagnostics(at: condition))
-    }.cast(ExprSyntax.self)
+    let (foldedCondition, foldingDiagnostics) = IfConfigClauseSyntax.foldOperators(condition)
 
     let (active, syntaxErrorsAllowed, evalDiagnostics) = evaluateIfConfig(
       condition: foldedCondition,
diff --git a/Sources/SwiftIfConfig/SyntaxProtocol+IfConfig.swift b/Sources/SwiftIfConfig/SyntaxProtocol+IfConfig.swift
index 7540d4a544e..4f87ad40877 100644
--- a/Sources/SwiftIfConfig/SyntaxProtocol+IfConfig.swift
+++ b/Sources/SwiftIfConfig/SyntaxProtocol+IfConfig.swift
@@ -57,10 +57,10 @@ extension SyntaxProtocol {
           // This was not the active clause, so we know that we're in an
           // inactive block. If syntax errors aren't allowable, this is an
           // unparsed region.
-          let (syntaxErrorsAllowed, localDiagnostics) = ifConfigClause.syntaxErrorsAllowed(
-            configuration: configuration
-          )
-          diagnostics.append(contentsOf: localDiagnostics)
+          let syntaxErrorsAllowed =
+            ifConfigClause.condition.map {
+              IfConfigClauseSyntax.syntaxErrorsAllowed($0).syntaxErrorsAllowed
+            } ?? false
 
           if syntaxErrorsAllowed {
             return (.unparsed, diagnostics)