diff --git a/src/rustc/middle/ty.rs b/src/rustc/middle/ty.rs
index 9a3d00e33d9..50730d0ed86 100644
--- a/src/rustc/middle/ty.rs
+++ b/src/rustc/middle/ty.rs
@@ -915,26 +915,57 @@ fn type_needs_unwind_cleanup(cx: ctxt, ty: t) -> bool {
       none { }
     }
 
-    // Prevent infinite recursion
-    cx.needs_unwind_cleanup_cache.insert(ty, false);
+    let tycache = new_ty_hash();
+    let needs_unwind_cleanup =
+        type_needs_unwind_cleanup_(cx, ty, tycache, false);
+    cx.needs_unwind_cleanup_cache.insert(ty, needs_unwind_cleanup);
+    ret needs_unwind_cleanup;
+}
 
+fn type_needs_unwind_cleanup_(cx: ctxt, ty: t,
+                              tycache: map::hashmap<t, ()>,
+                              encountered_box: bool) -> bool {
+
+    // Prevent infinite recursion
+    alt tycache.find(ty) {
+      some(_) { ret false; }
+      none { tycache.insert(ty, ()); }
+    }
+
+    let mut encountered_box = encountered_box;
     let mut needs_unwind_cleanup = false;
     maybe_walk_ty(ty) {|ty|
         alt get(ty).struct {
+          ty_box(_) | ty_opaque_box {
+            encountered_box = true;
+            true
+          }
           ty_nil | ty_bot | ty_bool |
           ty_int(_) | ty_uint(_) | ty_float(_) |
-          ty_box(_) | ty_rec(_) | ty_tup(_) {
+          ty_rec(_) | ty_tup(_) | ty_ptr(_) {
             true
           }
           ty_enum(did, tps) {
             for v in *enum_variants(cx, did) {
                 for aty in v.args {
                     let t = substitute_type_params(cx, tps, aty);
-                    needs_unwind_cleanup |= type_needs_unwind_cleanup(cx, t);
+                    needs_unwind_cleanup |=
+                        type_needs_unwind_cleanup_(cx, t, tycache,
+                                                   encountered_box);
                 }
             }
             !needs_unwind_cleanup
           }
+          ty_uniq(_) | ty_str | ty_vec(_) | ty_res(_, _, _) {
+            // Once we're inside a box, the annihilator will find
+            // it and destroy it.
+            if !encountered_box {
+                needs_unwind_cleanup = true;
+                false
+            } else {
+                true
+            }
+          }
           _ {
             needs_unwind_cleanup = true;
             false
@@ -942,8 +973,6 @@ fn type_needs_unwind_cleanup(cx: ctxt, ty: t) -> bool {
         }
     }
 
-    cx.needs_unwind_cleanup_cache.insert(ty, needs_unwind_cleanup);
-
     ret needs_unwind_cleanup;
 }
 
diff --git a/src/test/run-fail/unwind-box-fn-unique.rs b/src/test/run-fail/unwind-box-fn-unique.rs
new file mode 100644
index 00000000000..b164338c63c
--- /dev/null
+++ b/src/test/run-fail/unwind-box-fn-unique.rs
@@ -0,0 +1,14 @@
+// error-pattern:fail
+
+fn failfn() {
+    fail;
+}
+
+fn main() {
+    let y = ~0;
+    let x = @fn~() {
+        log(error, y);
+    };
+    failfn();
+    log(error, x);
+}
\ No newline at end of file
diff --git a/src/test/run-fail/unwind-box-fn.rs b/src/test/run-fail/unwind-box-fn.rs
new file mode 100644
index 00000000000..645822f292b
--- /dev/null
+++ b/src/test/run-fail/unwind-box-fn.rs
@@ -0,0 +1,14 @@
+// error-pattern:fail
+
+fn failfn() {
+    fail;
+}
+
+fn main() {
+    let y = ~0;
+    let x = @fn@() {
+        log(error, y);
+    };
+    failfn();
+    log(error, x);
+}
\ No newline at end of file
diff --git a/src/test/run-fail/unwind-box-iface.rs b/src/test/run-fail/unwind-box-iface.rs
new file mode 100644
index 00000000000..b9c674bd008
--- /dev/null
+++ b/src/test/run-fail/unwind-box-iface.rs
@@ -0,0 +1,19 @@
+// error-pattern:fail
+
+fn failfn() {
+    fail;
+}
+
+iface i {
+    fn foo();
+}
+
+impl of i for ~int {
+    fn foo() { }
+}
+
+fn main() {
+    let x = ~0 as i;
+    failfn();
+    log(error, x);
+}
\ No newline at end of file
diff --git a/src/test/run-fail/unwind-box-res.rs b/src/test/run-fail/unwind-box-res.rs
new file mode 100644
index 00000000000..e076f891031
--- /dev/null
+++ b/src/test/run-fail/unwind-box-res.rs
@@ -0,0 +1,18 @@
+// error-pattern:fail
+
+fn failfn() {
+    fail;
+}
+
+resource r(v: *int) unsafe {
+    let v2: ~int = unsafe::reinterpret_cast(v);
+}
+
+fn main() unsafe {
+    let i1 = ~0;
+    let i1p = unsafe::reinterpret_cast(i1);
+    unsafe::forget(i1);
+    let x = @r(i1p);
+    failfn();
+    log(error, x);
+}
\ No newline at end of file
diff --git a/src/test/run-fail/unwind-box-str.rs b/src/test/run-fail/unwind-box-str.rs
new file mode 100644
index 00000000000..e0cd34b784b
--- /dev/null
+++ b/src/test/run-fail/unwind-box-str.rs
@@ -0,0 +1,11 @@
+// error-pattern:fail
+
+fn failfn() {
+    fail;
+}
+
+fn main() {
+    let x = @"hi";
+    failfn();
+    log(error, x);
+}
\ No newline at end of file
diff --git a/src/test/run-fail/unwind-box-unique-unique.rs b/src/test/run-fail/unwind-box-unique-unique.rs
new file mode 100644
index 00000000000..023910eeecd
--- /dev/null
+++ b/src/test/run-fail/unwind-box-unique-unique.rs
@@ -0,0 +1,11 @@
+// error-pattern:fail
+
+fn failfn() {
+    fail;
+}
+
+fn main() {
+    let x = @~~0;
+    failfn();
+    log(error, x);
+}
\ No newline at end of file
diff --git a/src/test/run-fail/unwind-box-unique.rs b/src/test/run-fail/unwind-box-unique.rs
new file mode 100644
index 00000000000..18ed2768fa8
--- /dev/null
+++ b/src/test/run-fail/unwind-box-unique.rs
@@ -0,0 +1,11 @@
+// error-pattern:fail
+
+fn failfn() {
+    fail;
+}
+
+fn main() {
+    let x = @~0;
+    failfn();
+    log(error, x);
+}
\ No newline at end of file
diff --git a/src/test/run-fail/unwind-box-vec.rs b/src/test/run-fail/unwind-box-vec.rs
new file mode 100644
index 00000000000..7aa411ab017
--- /dev/null
+++ b/src/test/run-fail/unwind-box-vec.rs
@@ -0,0 +1,11 @@
+// error-pattern:fail
+
+fn failfn() {
+    fail;
+}
+
+fn main() {
+    let x = @[0, 1, 2, 3, 4, 5];
+    failfn();
+    log(error, x);
+}
\ No newline at end of file