diff --git a/lib/ocaml/eval.sx b/lib/ocaml/eval.sx
index e1b67468..87e55790 100644
--- a/lib/ocaml/eval.sx
+++ b/lib/ocaml/eval.sx
@@ -592,8 +592,9 @@
                       (loop)))))
               nil)))
         ((= tag "try")
-          ;; (:try EXPR CLAUSES) — evaluate EXPR; if it raises, match the
-          ;; raised value against CLAUSES. Re-raise on no-match.
+          ;; (:try EXPR CLAUSES) — evaluate EXPR; if it raises, match
+          ;; the raised value against CLAUSES (case + case-when).
+          ;; Re-raise on no-match.
           (let ((expr (nth ast 1)) (clauses (nth ast 2)) (env-cap env))
             (guard (e
                     (else
@@ -604,13 +605,26 @@
                               ((empty? cs) (raise e))
                               (else
                                 (let ((clause (first cs)))
-                                  (let ((pat (nth clause 1))
-                                        (body (nth clause 2)))
-                                    (let ((env2 (ocaml-match-pat pat e env-cap)))
-                                      (cond
-                                        ((= env2 ocaml-match-fail)
-                                          (try-clauses (rest cs)))
-                                        (else (ocaml-eval body env2))))))))))
+                                  (let ((ctag (nth clause 0)))
+                                    (cond
+                                      ((= ctag "case")
+                                        (let ((pat (nth clause 1))
+                                              (body (nth clause 2)))
+                                          (let ((env2 (ocaml-match-pat pat e env-cap)))
+                                            (cond
+                                              ((= env2 ocaml-match-fail)
+                                                (try-clauses (rest cs)))
+                                              (else (ocaml-eval body env2))))))
+                                      ((= ctag "case-when")
+                                        (let ((pat (nth clause 1))
+                                              (g (nth clause 2))
+                                              (body (nth clause 3)))
+                                          (let ((env2 (ocaml-match-pat pat e env-cap)))
+                                            (cond
+                                              ((= env2 ocaml-match-fail) (try-clauses (rest cs)))
+                                              ((not (ocaml-eval g env2)) (try-clauses (rest cs)))
+                                              (else (ocaml-eval body env2))))))
+                                      (else (raise e)))))))))
                         (try-clauses clauses))))
               (ocaml-eval expr env-cap))))
         ((= tag "while")
diff --git a/lib/ocaml/parser.sx b/lib/ocaml/parser.sx
index cfbff29f..e425d6e4 100644
--- a/lib/ocaml/parser.sx
+++ b/lib/ocaml/parser.sx
@@ -773,11 +773,18 @@
                   (begin
                     (define one
                       (fn ()
-                        (let ((p (parse-pattern)))
+                        (let ((p (parse-pattern)) (guard nil))
                           (begin
+                            (when (at-kw? "when")
+                              (begin (advance-tok!)
+                                     (set! guard (parse-expr-no-seq))))
                             (consume! "op" "->")
                             (let ((body (parse-expr)))
-                              (append! cases (list :case p body)))))))
+                              (cond
+                                ((= guard nil)
+                                  (append! cases (list :case p body)))
+                                (else
+                                  (append! cases (list :case-when p guard body)))))))))
                     (one)
                     (define loop
                       (fn ()
diff --git a/lib/ocaml/test.sh b/lib/ocaml/test.sh
index 1501d238..bb87b15e 100755
--- a/lib/ocaml/test.sh
+++ b/lib/ocaml/test.sh
@@ -1148,6 +1148,14 @@ cat > "$TMPFILE" << 'EPOCHS'
 (epoch 4402)
 (eval "(ocaml-run \"(function | n when n > 0 -> 1 | n when n < 0 -> -1 | _ -> 0) 0\")")
 
+;; ── try/with `when` guard ─────────────────────────────────────
+(epoch 4500)
+(eval "(ocaml-run \"try raise (E 5) with | E n when n > 0 -> n | _ -> 0\")")
+(epoch 4501)
+(eval "(ocaml-run \"try raise (E (-3)) with | E n when n > 0 -> n | _ -> 0\")")
+(epoch 4502)
+(eval "(ocaml-run \"try raise (E 5) with | E n when n > 100 -> n | E n -> n + 1000\")")
+
 EPOCHS
 
 OUTPUT=$(timeout 180 "$SX_SERVER" < "$TMPFILE" 2>/dev/null)
@@ -1818,6 +1826,11 @@ check 4400 "function when 5"              '1'
 check 4401 "function when -3"             '0'
 check 4402 "function sign 0"              '0'
 
+# ── try/with `when` guard ──────────────────────────────────────
+check 4500 "try when guard fires"         '5'
+check 4501 "try when guard skips"         '0'
+check 4502 "try when fall through"        '1005'
+
 TOTAL=$((PASS + FAIL))
 if [ $FAIL -eq 0 ]; then
   echo "ok $PASS/$TOTAL OCaml-on-SX tests passed"
diff --git a/plans/ocaml-on-sx.md b/plans/ocaml-on-sx.md
index 7d0d292e..64922541 100644
--- a/plans/ocaml-on-sx.md
+++ b/plans/ocaml-on-sx.md
@@ -407,6 +407,10 @@ _Newest first._
   binary search tree (`type 'a tree = Leaf | Node of 'a * 'a tree *
   'a tree`) with insert + in-order traversal. Tests parametric ADT,
   recursive match, List.append, List.fold_left.
+- 2026-05-08 Phase 2+3 — `try ... with | pat when GUARD -> body` guard
+  support (+3 tests, 467 total). parse-try mirrors match/function;
+  eval-try clause loop now dispatches on `case`/`case-when` and falls
+  through to next clause when guard is false.
 - 2026-05-08 Phase 1+3 — `function | pat when GUARD -> body | …`
   guard support (+3 tests, 464 total). `parse-function` mirrors the
   match-clause when-handling.