From a9395e9f73161da9583e82ebaf78012355ce980d Mon Sep 17 00:00:00 2001
From: TowyTowy <85077986+TowyTowy@users.noreply.github.com>
Date: Tue, 4 Aug 2026 20:46:28 +0200
Subject: [PATCH] fix: derive jwt signing key from users in a stable order
 (#4886)

Co-authored-by: Claude <noreply@anthropic.com>
---
 internal/auth/simple.go      |  9 ++++++-
 internal/auth/simple_test.go | 50 ++++++++++++++++++++++++++++++++++++
 2 files changed, 58 insertions(+), 1 deletion(-)
 create mode 100644 internal/auth/simple_test.go

diff --git a/internal/auth/simple.go b/internal/auth/simple.go
index 90cb7723..3e4bc658 100644
--- a/internal/auth/simple.go
+++ b/internal/auth/simple.go
@@ -3,7 +3,9 @@ package auth
 import (
 	"crypto/sha256"
 	"errors"
+	"maps"
 	"net/http"
+	"slices"
 	"time"
 
 	"github.com/go-chi/jwtauth/v5"
@@ -18,8 +20,13 @@ type simpleAuthContext struct {
 var ErrInvalidCredentials = errors.New("invalid credentials")
 
 func NewSimpleAuth(userDatabase UserDatabase, ttl time.Duration) *simpleAuthContext {
+	// Hash the users in a stable order. Ranging over the map directly makes the
+	// digest depend on Go's randomized map iteration order, so any users.yml with
+	// more than one user derives a different signing key on every start and
+	// silently invalidates every session on restart.
 	h := sha256.New()
-	for _, user := range userDatabase.Users {
+	for _, username := range slices.Sorted(maps.Keys(userDatabase.Users)) {
+		user := userDatabase.Users[username]
 		h.Write([]byte(user.Password))
 		h.Write([]byte(user.RolesConfigured))
 	}
diff --git a/internal/auth/simple_test.go b/internal/auth/simple_test.go
new file mode 100644
index 00000000..c48d6d21
--- /dev/null
+++ b/internal/auth/simple_test.go
@@ -0,0 +1,50 @@
+package auth
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+// The JWT signing key is derived from the users in users.yml so that a token
+// stays valid across restarts and is only invalidated when a password or role
+// actually changes. Deriving it by ranging over the user map made the digest
+// depend on Go's randomized map iteration order, so every restart of a
+// multi-user setup rolled the key and logged everyone out.
+func TestSimpleAuthSigningKeyIsStableAcrossRestarts(t *testing.T) {
+	users := UserDatabase{
+		Users: map[string]*User{
+			"alice": {Username: "alice", Password: "$2a$11$aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa", RolesConfigured: "all"},
+			"bob":   {Username: "bob", Password: "$2a$11$bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb", RolesConfigured: "shell"},
+			"carol": {Username: "carol", Password: "$2a$11$cccccccccccccccccccccccccccccccccccccccccccccccccccccc", RolesConfigured: "actions"},
+			"dave":  {Username: "dave", Password: "$2a$11$dddddddddddddddddddddddddddddddddddddddddddddddddddddd", RolesConfigured: "download"},
+		},
+	}
+
+	_, token, err := NewSimpleAuth(users, 0).tokenAuth.Encode(map[string]any{"username": "alice"})
+	require.NoError(t, err)
+
+	// Each iteration stands in for a Dozzle restart against an unchanged users.yml.
+	for i := range 50 {
+		if _, err := NewSimpleAuth(users, 0).tokenAuth.Decode(token); err != nil {
+			t.Fatalf("token issued before restart %d was rejected: %v", i+1, err)
+		}
+	}
+}
+
+// Changing a password or a role must still roll the key so old tokens stop working.
+func TestSimpleAuthSigningKeyChangesWhenCredentialsChange(t *testing.T) {
+	users := UserDatabase{
+		Users: map[string]*User{
+			"alice": {Username: "alice", Password: "$2a$11$aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa", RolesConfigured: "all"},
+			"bob":   {Username: "bob", Password: "$2a$11$bbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbbb", RolesConfigured: "shell"},
+		},
+	}
+
+	_, token, err := NewSimpleAuth(users, 0).tokenAuth.Encode(map[string]any{"username": "alice"})
+	require.NoError(t, err)
+
+	users.Users["bob"].RolesConfigured = "shell,actions"
+	_, err = NewSimpleAuth(users, 0).tokenAuth.Decode(token)
+	require.Error(t, err)
+}