diff --git a/backend/internal/auth/middleware_test.go b/backend/internal/auth/middleware_test.go
index c6733ed..2a4de0d 100644
--- a/backend/internal/auth/middleware_test.go
+++ b/backend/internal/auth/middleware_test.go
@@ -63,7 +63,7 @@ func TestRequireSession_TamperedCookie(t *testing.T) {
 	if err != nil {
 		t.Fatalf("mint: %v", err)
 	}
-	cookie.Value = flipLastChar(cookie.Value)
+	cookie.Value = flipSignatureChar(cookie.Value)
 	req := httptest.NewRequest(http.MethodGet, "/", nil)
 	req.AddCookie(cookie)
 	rec := httptest.NewRecorder()
diff --git a/backend/internal/auth/session_test.go b/backend/internal/auth/session_test.go
index fbfaf5a..702e963 100644
--- a/backend/internal/auth/session_test.go
+++ b/backend/internal/auth/session_test.go
@@ -41,25 +41,38 @@ func TestParseSessionCookie_Tampered(t *testing.T) {
 	if err != nil {
 		t.Fatalf("mint: %v", err)
 	}
-	cookie.Value = flipLastChar(cookie.Value)
+	cookie.Value = flipSignatureChar(cookie.Value)
 	if _, err := ParseSessionCookie(cookie, []byte(testSecret)); err == nil {
 		t.Fatal("expected error for tampered cookie")
 	}
 }
 
-// flipLastChar corrupts a signed token for tamper tests, guaranteeing the
-// last character actually changes -- blindly overwriting it with a fixed
-// character (e.g. "x") would occasionally be a no-op if that character
-// already happened to be there (it's derived from the token's embedded
-// timestamp, so this isn't as rare as it sounds), silently passing the
-// test without having tampered with anything.
-func flipLastChar(s string) string {
-	last := s[len(s)-1]
+// flipSignatureChar corrupts a signed JWT for tamper tests by changing the
+// second-to-last character of its base64url signature, guaranteeing the
+// decoded signature bytes actually change. Two pitfalls to avoid here:
+//  1. Blindly overwriting a character with a fixed replacement (e.g. "x")
+//     would occasionally be a no-op if that character was already there --
+//     it's derived from the token's embedded timestamp, so this isn't as
+//     rare as it sounds.
+//  2. Flipping the *last* character of the signature specifically (as this
+//     helper used to) is flaky in a subtler way: HMAC-SHA256 produces a
+//     32-byte digest, which base64url-encodes to 43 characters with a
+//     final 3-character group covering only a 2-byte remainder -- the
+//     true last character encodes 4 real bits plus 2 unused padding bits.
+//     Go's encoding/base64 ignores those padding bits when decoding
+//     (non-strict by default), so about 1 in 4 replacement characters for
+//     that position decode to byte-identical signature bytes, silently
+//     passing the test without having tampered with anything. The
+//     second-to-last character of that final group has no such unused
+//     bits, so corrupting it is deterministic.
+func flipSignatureChar(s string) string {
+	pos := len(s) - 2
+	orig := s[pos]
 	replacement := byte('x')
-	if last == replacement {
+	if orig == replacement {
 		replacement = 'y'
 	}
-	return s[:len(s)-1] + string(replacement)
+	return s[:pos] + string(replacement) + s[pos+1:]
 }
 
 func TestParseSessionCookie_WrongSecret(t *testing.T) {