diff --git a/collects/typed-scheme/optimizer/logging.rkt b/collects/typed-scheme/optimizer/logging.rkt
index 06f26eb1..b9e861ab 100644
--- a/collects/typed-scheme/optimizer/logging.rkt
+++ b/collects/typed-scheme/optimizer/logging.rkt
@@ -1,7 +1,7 @@
 #lang racket/base
 
-(require racket/set racket/string racket/match racket/list
-         unstable/syntax unstable/logging
+(require racket/set racket/string racket/match racket/list racket/serialize
+         unstable/syntax unstable/logging syntax/to-string
          "../utils/tc-utils.rkt")
 
 (provide log-optimization log-missed-optimization
@@ -10,7 +10,8 @@
          with-intercepted-tr-logging with-tr-logging-to-port
          (struct-out log-entry)
          (struct-out opt-log-entry)
-         (struct-out missed-opt-log-entry))
+         (struct-out missed-opt-log-entry)
+         (struct-out pseudo-syntax))
 
 ;;--------------------------------------------------------------------
 
@@ -26,11 +27,29 @@
 (define log-so-far '())
 
 ;; msg is for consumption by the DrRacket tool
-(struct log-entry (kind msg stx located-stx pos) #:prefab)
+;; mutability is there only to replace syntax with pseudo-syntax before
+;; printing at the end
+(struct log-entry (kind msg (stx #:mutable) (located-stx #:mutable) pos)
+        #:prefab)
 ;; for optimizations only (not missed optimizations, those are below)
 (struct opt-log-entry log-entry () #:prefab)
 
 
+;; syntax objects are not serializable.
+;; this is a prefab struct that holds the information we need from syntax
+;; objects while still being serializable
+;; rep : string (result of syntax->string)
+(struct pseudo-syntax (rep line column position span
+                       source-directory source-file-name)
+        #:prefab)
+(define (syntax->pseudo-syntax stx)
+  (pseudo-syntax (syntax->string #`(#,stx)) ; takes a list of stxs
+                 (syntax-line stx) (syntax-column stx)
+                 (syntax-position stx) (syntax-span stx)
+                 (serialize (syntax-source-directory stx))
+                 (serialize (syntax-source-file-name stx))))
+
+
 (define (log-optimization kind msg stx)
   (let ([new-entry
          (opt-log-entry kind msg
@@ -53,7 +72,7 @@
 ;; that got merged into this miss. we need to keep them around to detect
 ;; future potential merges.
 (struct missed-opt-log-entry log-entry
-        (irritants merged-irritants badness)
+        ((irritants #:mutable) (merged-irritants #:mutable) badness)
         #:prefab)
 
 (define missed-optimizations-log '())
@@ -214,8 +233,18 @@
   (define logger (current-logger))
   (add-missed-opts-to-log)
   (for ([x (sort-log)])
-    (log-message logger 'warning
-                 (format-log-entry x)
+    (define out (format-log-entry x))
+    (set-log-entry-stx!         x (syntax->pseudo-syntax (log-entry-stx x)))
+    (set-log-entry-located-stx! x (syntax->pseudo-syntax
+                                   (log-entry-located-stx x)))
+    (when (missed-opt-log-entry? x)
+      (set-missed-opt-log-entry-irritants!
+       x (map syntax->pseudo-syntax
+              (missed-opt-log-entry-irritants x)))
+      (set-missed-opt-log-entry-merged-irritants!
+       x (map syntax->pseudo-syntax
+              (missed-opt-log-entry-merged-irritants x))))
+    (log-message logger 'warning out
                  (cons optimization-log-key x))))
 
 (define (clear-log)