diff --git a/lib/Sema/CSSimplify.cpp b/lib/Sema/CSSimplify.cpp
index fa8b19072360d..2550170bb7cad 100644
--- a/lib/Sema/CSSimplify.cpp
+++ b/lib/Sema/CSSimplify.cpp
@@ -5365,6 +5365,11 @@ bool ConstraintSystem::repairFailures(
       matchKind = ConstraintKind::Conversion;
     }
 
+    // FIXME: There is currently no easy way to avoid attempting
+    // fixes, matchTypes do not propagate `TMF_ApplyingFix` flag.
+    llvm::SaveAndRestore<ConstraintSystemOptions> options(
+        Options, Options - ConstraintSystemFlags::AllowFixes);
+
     auto result = matchTypes(resultType, dstType, matchKind,
                              TypeMatchFlags::TMF_ApplyingFix, locator);
 
diff --git a/test/Constraints/assignment.swift b/test/Constraints/assignment.swift
index 4ccdf8951bee3..f97b7e4c25031 100644
--- a/test/Constraints/assignment.swift
+++ b/test/Constraints/assignment.swift
@@ -88,3 +88,16 @@ class С_56396 {
     self.callback = callback // expected-error {{cannot assign value of type '(Self) -> Void' to type '(С_56396) -> Void'}}
   }
 }
+
+// https://github.com/swiftlang/swift/issues/82397
+func testFunctionAssignsWithOptionals(fn: @escaping () -> () -> Void) {
+  let _: (() -> () -> Void)? = fn
+  let _: (() -> () -> Void)?? = fn
+
+  class Super {}
+  class Sub: Super {}
+
+  let b: () -> () -> Sub = { { return Sub() } }
+  let _: (() -> () -> Super)? = b
+  let _: (() -> () -> Super)?? = b
+}