diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/union.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/union.rkt
index 19f67817..16b7b7d4 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/union.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/union.rkt
@@ -3,7 +3,7 @@
 (require "../utils/utils.rkt"
          (rep type-rep rep-utils)
          (prefix-in c: (contract-req))
-         (types subtype base-abbrev resolve)
+         (types subtype base-abbrev resolve current-seen)
          racket/match
          racket/list)
 
@@ -21,6 +21,8 @@
 ;; a is a Type (not a union type)
 ;; b is a List[Type] (non overlapping, non Union-types)
 ;; The output is a non overlapping list of non Union types.
+;; The overlapping constraint is lifted if we are in the midst of subtyping. This is because during
+;; subtyping calls to subtype are expensive.
 (define (merge a b)
   (define b* (make-union* b))
   (match* (a b)
@@ -32,6 +34,7 @@
      ;; so that bad applications are rejected early.
      (resolve-app-check-error rator rands stx)
      (cons a b)]
+    [(_ _) #:when (currently-subtyping?) (cons a b)]
     [((? (λ _ (subtype a b*))) _) b]
     [((? (λ _ (subtype b* a))) _) (list a)]
     [(_ _) (cons a (filter-not (λ (b-elem) (subtype b-elem a)) b))]))
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/succeed/pr14582.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/succeed/pr14582.rkt
new file mode 100644
index 00000000..c1eea266
--- /dev/null
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/succeed/pr14582.rkt
@@ -0,0 +1,34 @@
+#lang typed/racket/base
+(define-type CodeOfBoolean (Code Boolean))
+(define-type CodeOfInteger (Code Integer))
+(define-type CodeOfAny
+  (U CodeOfInteger
+     CodeOfBoolean))
+
+(define-type (Code Type)
+  (U Type
+     (If Type)
+     (Begin Type)))
+
+
+(struct (Type) If
+  ([cond : CodeOfBoolean]
+   [then : (Code Type)]
+   [else : (Code Type)])
+  #:transparent)
+
+
+
+(define-type (ListEndingIn ListType EndType)
+  (U (Pair EndType Null)
+     (Pair ListType (ListEndingIn ListType EndType))))
+
+(struct (Type) Begin
+  ([exprs : (ListEndingIn CodeOfAny (Code Type))]))
+
+
+(define QuotedCode : CodeOfInteger
+  (If #t
+      1
+      (Begin
+       (list 2 #f (If #t 3 4)))))