diff --git a/typed-racket-lib/typed-racket/infer/intersect.rkt b/typed-racket-lib/typed-racket/infer/intersect.rkt
index e6f4c3fa..f3be5875 100644
--- a/typed-racket-lib/typed-racket/infer/intersect.rkt
+++ b/typed-racket-lib/typed-racket/infer/intersect.rkt
@@ -51,15 +51,15 @@
      
          ;; structural recursion on types
          [((Pair: a1 d1) (Pair: a2 d2))
-          (-pair (rec a1 a2) (rec d1 d2))]
+          (rebuild -pair (rec a1 a2) (rec d1 d2))]
          ;; FIXME: support structural updating for structs when structs are updated to
          ;; contain not only *if* they are polymorphic, but *which* fields are too
          ;;[((Struct: _ _ _ _ _ _)
          ;; (Struct: _ _ _ _ _ _))]
          [((Syntax: t1*) (Syntax: t2*))
-          (-Syntax (rec t1* t2*))]
+          (rebuild -Syntax (rec t1* t2*))]
          [((Promise: t1*) (Promise: t2*))
-          (-Promise (rec t1* t2*))]
+          (rebuild -Promise (rec t1* t2*))]
 
          [((Union: t1s) t2)
           (match t2
@@ -130,9 +130,6 @@
 ;; and sometimes we want to make sure and _not_ add t2 to the result
 ;; we just want to keep the parts of t1 consistent with t2)
 (define (restrict t1 t2)
-  ;; build-type: build a type while propogating bottom
-  (define (build-type constructor . args)
-    (if (memf Bottom? args) -Bottom (apply constructor args)))
   ;; resolved is a set tracking previously seen restrict cases
   ;; (i.e. pairs of t1 t2) to prevent infinite unfolding.
   ;; subtyping performs a similar check for the same
@@ -150,17 +147,17 @@
       
       ;; structural recursion on types
       [((Pair: a1 d1) (Pair: a2 d2)) 
-       (build-type -pair 
-                   (restrict a1 a2 resolved) 
-                   (restrict d1 d2 resolved))]
+       (rebuild -pair
+                (restrict a1 a2 resolved)
+                (restrict d1 d2 resolved))]
       ;; FIXME: support structural updating for structs when structs are updated to
       ;; contain not only *if* they are polymorphic, but *which* fields are too  
       ;;[((Struct: _ _ _ _ _ _)
       ;; (Struct: _ _ _ _ _ _))]
       [((Syntax: t1*) (Syntax: t2*))
-       (build-type -Syntax (restrict t1* t2* resolved))]
+       (rebuild -Syntax (restrict t1* t2* resolved))]
       [((Promise: t1*) (Promise: t2*))
-       (build-type -Promise (restrict t1* t2* resolved))]
+       (rebuild -Promise (restrict t1* t2* resolved))]
       
       ;; unions
       [((Union: t1s) t2)
diff --git a/typed-racket-lib/typed-racket/rep/type-rep.rkt b/typed-racket-lib/typed-racket/rep/type-rep.rkt
index 205e7719..eae71e50 100644
--- a/typed-racket-lib/typed-racket/rep/type-rep.rkt
+++ b/typed-racket-lib/typed-racket/rep/type-rep.rkt
@@ -199,11 +199,7 @@
 ;; left and right are Types
 (def-structural Pair ([left #:covariant]
                       [right #:covariant])
-  [#:mask mask:pair]
-  [#:custom-constructor
-   (if (or (Bottom? left) (Bottom? right))
-       -Bottom
-       (make-Pair left right))])
+  [#:mask mask:pair])
 
 ;;----------------
 ;; Mutable Pairs
@@ -216,11 +212,7 @@
 ;; *mutable* pairs - distinct from regular pairs
 ;; left and right are Types
 (def-structural MPair ([left #:invariant] [right #:invariant])
-  [#:mask mask:mpair]
-  [#:custom-constructor
-   (if (or (Bottom? left) (Bottom? right))
-       -Bottom
-       (make-MPair left right))])
+  [#:mask mask:mpair])
 
 ;;----------
 ;; Vectors
@@ -242,11 +234,7 @@
   [#:singleton -BoxTop])
 
 (def-structural Box ([elem #:invariant])
-  [#:mask mask:box]
-  [#:custom-constructor
-   (if (Bottom? elem)
-       -Bottom
-       (make-Box elem))])
+  [#:mask mask:box])
 
 ;;----------
 ;; Channel
@@ -257,11 +245,7 @@
   [#:singleton -ChannelTop])
 
 (def-structural Channel ([elem #:invariant])
-  [#:mask mask:channel]
-  [#:custom-constructor
-   (if (Bottom? elem)
-       -Bottom
-       (make-Channel elem))])
+  [#:mask mask:channel])
 
 ;;----------------
 ;; Async-Channel
@@ -272,11 +256,7 @@
   [#:singleton -Async-ChannelTop])
 
 (def-structural Async-Channel ([elem #:invariant])
-  [#:mask mask:channel]
-  [#:custom-constructor
-   (if (Bottom? elem)
-       -Bottom
-       (make-Async-Channel elem))])
+  [#:mask mask:channel])
 
 ;;-------------
 ;; ThreadCell
@@ -287,33 +267,21 @@
   [#:singleton -ThreadCellTop])
 
 (def-structural ThreadCell ([elem #:invariant])
-  [#:mask mask:thread-cell]
-  [#:custom-constructor
-   (if (Bottom? elem)
-       -Bottom
-       (make-ThreadCell elem))])
+  [#:mask mask:thread-cell])
 
 ;;----------
 ;; Promise
 ;;----------
 
 (def-structural Promise ([elem #:covariant])
-  [#:mask mask:promise]
-  [#:custom-constructor
-   (if (Bottom? elem)
-       -Bottom
-       (make-Promise elem))])
+  [#:mask mask:promise])
 
 ;;------------
 ;; Ephemeron
 ;;------------
 
 (def-structural Ephemeron ([elem #:covariant])
-  [#:mask mask:ephemeron]
-  [#:custom-constructor
-   (if (Bottom? elem)
-       -Bottom
-       (make-Ephemeron elem))])
+  [#:mask mask:ephemeron])
 
 
 ;;-----------
@@ -325,11 +293,7 @@
   [#:singleton -Weak-BoxTop])
 
 (def-structural Weak-Box ([elem #:invariant])
-  [#:mask mask:other-box]
-  [#:custom-constructor
-   (if (Bottom? elem)
-       -Bottom
-       (make-Weak-Box elem))])
+  [#:mask mask:other-box])
 
 
 ;;---------------
@@ -337,11 +301,7 @@
 ;;---------------
 
 (def-structural CustodianBox ([elem #:covariant])
-  [#:mask mask:other-box]
-  [#:custom-constructor
-   (if (Bottom? elem)
-       -Bottom
-       (make-CustodianBox elem))])
+  [#:mask mask:other-box])
 
 ;;------
 ;; Set
@@ -385,22 +345,14 @@
 
 ;; t is the type of the result of syntax-e, not the result of syntax->datum
 (def-structural Syntax ([t #:covariant])
-  [#:mask mask:syntax]
-  [#:custom-constructor
-   (if (Bottom? t)
-       -Bottom
-       (make-Syntax t))])
+  [#:mask mask:syntax])
 
 ;;---------
 ;; Future
 ;;---------
 
 (def-structural Future ([t #:covariant])
-  [#:mask mask:future]
-  [#:custom-constructor
-   (if (Bottom? t)
-       -Bottom
-       (make-Future t))])
+  [#:mask mask:future])
 
 
 ;;---------------
@@ -417,11 +369,7 @@
 ;;   and the codomains of `handler`
 (def-structural Prompt-Tagof ([body #:invariant]
                               [handler #:invariant])
-  [#:mask mask:prompt-tag]
-  [#:custom-constructor
-   (if (or (Bottom? body) (Bottom? handler))
-       -Bottom
-       (make-Prompt-Tagof body handler))])
+  [#:mask mask:prompt-tag])
 
 ;;--------------------------
 ;; Continuation-Mark-Keyof
@@ -460,11 +408,7 @@
   [#:frees (f) (make-invariant (combine-frees (map f elems)))]
   [#:fmap (f) (make-HeterogeneousVector (map f elems))]
   [#:for-each (f) (for-each f elems)]
-  [#:mask mask:vector]
-  [#:custom-constructor
-   (if (ormap Bottom? elems)
-       -Bottom
-       (make-HeterogeneousVector elems))])
+  [#:mask mask:vector])
 
 
 ;; * * * * * * *
@@ -617,14 +561,12 @@
   ;; This should eventually be based on understanding of struct properties.
   [#:mask (mask-union mask:struct mask:procedure)]
   [#:custom-constructor
-   (cond
-     [(ormap (λ (fld) (Bottom? (fld-t fld))) flds) -Bottom]
-     [else (make-Struct (normalize-id name)
-                        parent
-                        flds
-                        proc
-                        poly?
-                        (normalize-id pred-id))])])
+   (make-Struct (normalize-id name)
+                parent
+                flds
+                proc
+                poly?
+                (normalize-id pred-id))])
 
 ;; Represents prefab structs
 ;; key  : prefab key encoding mutability, auto-fields, etc.
@@ -634,11 +576,7 @@
   [#:frees (f) (combine-frees (map f flds))]
   [#:fmap (f) (make-Prefab key (map f flds))]
   [#:for-each (f) (for-each f flds)]
-  [#:mask mask:prefab]
-  [#:custom-constructor
-   (cond
-     [(ormap Bottom? flds) -Bottom]
-     [else (make-Prefab key flds)])])
+  [#:mask mask:prefab])
 
 (def-type StructTypeTop ()
   [#:mask mask:struct-type]
@@ -772,10 +710,7 @@
   [#:fmap (f) (make-Refinement (f parent) pred)]
   [#:for-each (f) (f parent)]
   [#:mask (λ (t) (mask (Refinement-parent t)))]
-  [#:custom-constructor
-   (if (Bottom? parent)
-       -Bottom
-       (make-Refinement parent (normalize-id pred)))])
+  [#:custom-constructor (make-Refinement parent (normalize-id pred))])
 
 ;; A Row used in type instantiation
 ;; For now, this should not appear in user code. It's used
diff --git a/typed-racket-lib/typed-racket/types/base-abbrev.rkt b/typed-racket-lib/typed-racket/types/base-abbrev.rkt
index c1cc701c..b6538aff 100644
--- a/typed-racket-lib/typed-racket/types/base-abbrev.rkt
+++ b/typed-racket-lib/typed-racket/types/base-abbrev.rkt
@@ -22,6 +22,16 @@
          (rename-out [make-Listof -lst]
                      [make-MListof -mlst]))
 
+(define-syntax (rebuild stx)
+  (syntax-case stx ()
+    [(_ mk args ...)
+     (with-syntax ([(t ...) (generate-temporaries #'(args ...))])
+       (syntax/loc stx
+         (let ([t args] ...)
+           (if (or (Bottom? t) ...)
+               -Bottom
+               (mk t ...)))))]))
+
 (define/decl -False (make-Value #f))
 (define/decl -True (make-Value #t))
 (define/decl -Boolean (Un -False -True))
diff --git a/typed-racket-lib/typed-racket/types/update.rkt b/typed-racket-lib/typed-racket/types/update.rkt
index c6148416..2f6bde85 100644
--- a/typed-racket-lib/typed-racket/types/update.rkt
+++ b/typed-racket-lib/typed-racket/types/update.rkt
@@ -23,9 +23,6 @@
 ;;   in *syntactic order* (e.g. (car (cdr x)) -> '(car cdr))  
 (define/cond-contract (update t new-t pos? path-elems)
   (Type? Type? boolean? (listof PathElem?) . -> . Type?)
-  ;; build-type: build a type while propogating bottom
-  (define (build constructor . args)
-    (if (memf Bottom? args) -Bottom (apply constructor args)))
   ;; update's inner recursive loop
   ;; puts path in *accessed* order
   ;; (i.e. (car (cdr x)) --> (list cdr car))
@@ -38,15 +35,15 @@
        (match* ((resolve t) path-elem)
          ;; pair ops
          [((Pair: t s) (CarPE:))
-          (build -pair (update t rst) s)]
+          (rebuild -pair (update t rst) s)]
          [((Pair: t s) (CdrPE:))
-          (build -pair t (update s rst))]
+          (rebuild -pair t (update s rst))]
          ;; syntax ops
          [((Syntax: t) (SyntaxPE:))
-          (build -Syntax (update t rst))]
+          (rebuild -Syntax (update t rst))]
          ;; promise op
          [((Promise: t) (ForcePE:))
-          (build -Promise (update t rst))]
+          (rebuild -Promise (update t rst))]
          
          ;; struct ops
          [((Struct: nm par flds proc poly pred)
diff --git a/typed-racket-test/fail/issue-169-1.rkt b/typed-racket-test/fail/issue-169-1.rkt
index 125886d9..5f6eaa7c 100644
--- a/typed-racket-test/fail/issue-169-1.rkt
+++ b/typed-racket-test/fail/issue-169-1.rkt
@@ -1,5 +1,5 @@
 #;
-(exn-pred #rx"expected: \\Null.*given: \\(Listof Pos\\*\\)")
+(exn-pred #rx"expected: \\(Listof Nothing\\).*given: \\(Listof Pos\\*\\)")
 #lang typed/racket
 (define-type Pos Integer)
 (define-new-subtype Pos* (p Pos))
diff --git a/typed-racket-test/fail/issue-169-2.rkt b/typed-racket-test/fail/issue-169-2.rkt
index e38bd54f..fbb99eb0 100644
--- a/typed-racket-test/fail/issue-169-2.rkt
+++ b/typed-racket-test/fail/issue-169-2.rkt
@@ -1,5 +1,5 @@
 #;
-(exn-pred #rx"expected: \\Null.*given: \\(Listof Pos\\*\\)")
+(exn-pred #rx"expected: \\(Listof Nothing\\).*given: \\(Listof Pos\\*\\)")
 #lang typed/racket
 (define-type Pos Integer)
 (define-new-subtype Pos* (p Pos))
diff --git a/typed-racket-test/succeed/inf-nested-bot.rkt b/typed-racket-test/succeed/inf-nested-bot.rkt
new file mode 100644
index 00000000..12465507
--- /dev/null
+++ b/typed-racket-test/succeed/inf-nested-bot.rkt
@@ -0,0 +1,16 @@
+#lang typed/racket
+
+(define-type (Promiseof A) (Boxof (U (→ (Listof A)) (Listof A))))
+(struct: (A) Queue ([fld : (Promiseof A)]))
+
+(define-syntax-rule (empty A)
+  ((inst Queue A) (box (lambda: () '()))))
+
+(: empty? : (All (A) ((Queue A) -> Boolean)))
+(define (empty? q)
+  (null? (Queue-fld q)))
+
+;; make sure that inference works on nested 'Nothing' types
+(empty? (empty Nothing))
+
+