diff --git a/README.md b/README.md
index ad1256a..8e3d237 100644
--- a/README.md
+++ b/README.md
@@ -54,6 +54,20 @@ assert($x > 0, "x must be positive");
 # => x must be positive
 ```
 
+The message expression is lazily evaluated. It is only evaluated when the assertion fails.
+This is equivalent to:
+
+```
+$cond || do { die $msg }
+```
+
+This means you can use expensive computations or side effects in the message without worrying about performance when the assertion passes:
+
+```
+assert($x > 0, expensive_debug_info());
+# expensive_debug_info() is NOT called if $x > 0
+```
+
 # SEE ALSO
 
 - [PerlX::Assert](https://metacpan.org/pod/PerlX%3A%3AAssert)
diff --git a/lib/Syntax/Keyword/Assert.pm b/lib/Syntax/Keyword/Assert.pm
index e298313..cdb427b 100644
--- a/lib/Syntax/Keyword/Assert.pm
+++ b/lib/Syntax/Keyword/Assert.pm
@@ -87,6 +87,16 @@ You can provide a custom error message as the second argument:
     assert($x > 0, "x must be positive");
     # => x must be positive
 
+The message expression is lazily evaluated. It is only evaluated when the assertion fails.
+This is equivalent to:
+
+    $cond || do { die $msg }
+
+This means you can use expensive computations or side effects in the message without worrying about performance when the assertion passes:
+
+    assert($x > 0, expensive_debug_info());
+    # expensive_debug_info() is NOT called if $x > 0
+
 =head1 SEE ALSO
 
 =over 4
diff --git a/lib/Syntax/Keyword/Assert.xs b/lib/Syntax/Keyword/Assert.xs
index 6ec8890..97e513b 100644
--- a/lib/Syntax/Keyword/Assert.xs
+++ b/lib/Syntax/Keyword/Assert.xs
@@ -59,16 +59,12 @@ static OP *pp_assert(pTHX)
   croak_sv(msg);
 }
 
-static XOP xop_assert_msg;
-static OP *pp_assert_msg(pTHX)
+/* Called after msgop is evaluated to croak with the message */
+static XOP xop_assert_croak;
+static OP *pp_assert_croak(pTHX)
 {
   dSP;
   SV *custom_msg = POPs;
-  SV *val = POPs;
-
-  if(SvTRUE(val))
-    RETURN;
-
   croak_sv(custom_msg);
 }
 
@@ -187,9 +183,16 @@ static int build_assert(pTHX_ OP **out, XSParseKeywordPiece *args[], size_t narg
 
     if (assert_enabled) {
         if (msgop) {
-            // With custom message: use pp_assert_msg
-            // condop evaluates to true/false, msgop is the error message
-            *out = newBINOP_CUSTOM(&pp_assert_msg, 0, condop, msgop);
+            // With custom message: lazy evaluation using OP_OR
+            // assert(cond, msg) becomes: cond || do { croak(msg) }
+            //
+            // OP_OR: if condop is true, short-circuit; if false, evaluate other
+            // We use op_scope to isolate the other branch's op_next chain
+
+            OP *croakop     = newUNOP_CUSTOM(&pp_assert_croak, 0, msgop);
+            OP *scopedblock = op_scope(croakop);
+
+            *out = newLOGOP(OP_OR, 0, condop, scopedblock);
         }
         else {
             // Without custom message: check if binary operator for better error
@@ -248,10 +251,10 @@ BOOT:
   XopENTRY_set(&xop_assertbin, xop_class, OA_BINOP);
   Perl_custom_op_register(aTHX_ &pp_assertbin, &xop_assertbin);
 
-  XopENTRY_set(&xop_assert_msg, xop_name, "assert_msg");
-  XopENTRY_set(&xop_assert_msg, xop_desc, "assert with message");
-  XopENTRY_set(&xop_assert_msg, xop_class, OA_BINOP);
-  Perl_custom_op_register(aTHX_ &pp_assert_msg, &xop_assert_msg);
+  XopENTRY_set(&xop_assert_croak, xop_name, "assert_croak");
+  XopENTRY_set(&xop_assert_croak, xop_desc, "assert croak with message");
+  XopENTRY_set(&xop_assert_croak, xop_class, OA_UNOP);
+  Perl_custom_op_register(aTHX_ &pp_assert_croak, &xop_assert_croak);
 
   register_xs_parse_keyword("assert", &hooks_assert, NULL);
 
diff --git a/t/01_assert/custom_message.t b/t/01_assert/custom_message.t
index f58538b..b1914c3 100644
--- a/t/01_assert/custom_message.t
+++ b/t/01_assert/custom_message.t
@@ -60,6 +60,53 @@ subtest 'custom message with string comparison' => sub {
     ok lives { assert("a" lt "b", "This should not appear") };
 };
 
+subtest 'lazy evaluation of custom message' => sub {
+    subtest 'message not evaluated when condition is true' => sub {
+        my $evaluated = 0;
+        my $get_msg = sub { $evaluated++; return "should not see this" };
+
+        ok lives { assert(1, $get_msg->()) };
+        is $evaluated, 0, "message expression is NOT evaluated when condition is true";
+    };
+
+    subtest 'message evaluated when condition is false' => sub {
+        my $evaluated = 0;
+        my $get_msg = sub { $evaluated++; return "assertion failed!" };
+
+        like dies { assert(0, $get_msg->()) },
+            qr/assertion failed!/;
+        is $evaluated, 1, "message expression is evaluated when condition is false";
+    };
+
+    subtest 'expensive computation skipped when true' => sub {
+        my @log;
+        my $expensive = sub { push @log, "computed"; return "error msg" };
+
+        ok lives { assert("truthy value", $expensive->()) };
+        is scalar(@log), 0, "expensive computation skipped when condition is true";
+    };
+
+    subtest 'side effects only on false' => sub {
+        my $side_effect_count = 0;
+        my $msg_with_side_effect = sub {
+            $side_effect_count++;
+            return "Side effect triggered $side_effect_count times";
+        };
+
+        # Multiple true assertions - side effects should NOT happen
+        ok lives { assert(1, $msg_with_side_effect->()) };
+        ok lives { assert("yes", $msg_with_side_effect->()) };
+        ok lives { assert(100, $msg_with_side_effect->()) };
+
+        is $side_effect_count, 0, "no side effects when all conditions are true";
+
+        # Now a false assertion - side effect SHOULD happen
+        like dies { assert(0, $msg_with_side_effect->()) },
+            qr/Side effect triggered/;
+        is $side_effect_count, 1, "side effect happened on false assertion";
+    };
+};
+
 subtest 'custom message with variables' => sub {
     subtest 'basic' => sub {
         my $x = 0;