diff --git a/management/internals/shared/grpc/proxy.go b/management/internals/shared/grpc/proxy.go
index aae6ef2f9..cecde960d 100644
--- a/management/internals/shared/grpc/proxy.go
+++ b/management/internals/shared/grpc/proxy.go
@@ -3,6 +3,7 @@ package grpc
 import (
 	"context"
 	"crypto/hmac"
+	"crypto/rand"
 	"crypto/sha256"
 	"encoding/base64"
 	"encoding/hex"
@@ -747,10 +748,20 @@ func (s *ProxyServiceServer) GetOIDCURL(ctx context.Context, req *proto.GetOIDCU
 		scopes = []string{oidc.ScopeOpenID, "profile", "email"}
 	}
 
+	// Generate a random nonce to ensure each OIDC request gets a unique state.
+	// Without this, multiple requests to the same URL would generate the same state
+	// but different PKCE verifiers, causing the later verifier to overwrite the earlier one.
+	nonce := make([]byte, 16)
+	if _, err := rand.Read(nonce); err != nil {
+		return nil, status.Errorf(codes.Internal, "generate nonce: %v", err)
+	}
+	nonceB64 := base64.URLEncoding.EncodeToString(nonce)
+
 	// Using an HMAC here to avoid redirection state being modified.
-	// State format: base64(redirectURL)|hmac
-	hmacSum := s.generateHMAC(redirectURL.String())
-	state := fmt.Sprintf("%s|%s", base64.URLEncoding.EncodeToString([]byte(redirectURL.String())), hmacSum)
+	// State format: base64(redirectURL)|nonce|hmac(redirectURL|nonce)
+	payload := redirectURL.String() + "|" + nonceB64
+	hmacSum := s.generateHMAC(payload)
+	state := fmt.Sprintf("%s|%s|%s", base64.URLEncoding.EncodeToString([]byte(redirectURL.String())), nonceB64, hmacSum)
 
 	codeVerifier := oauth2.GenerateVerifier()
 	s.pkceVerifiers.Store(state, pkceEntry{verifier: codeVerifier, createdAt: time.Now()})
@@ -803,13 +814,15 @@ func (s *ProxyServiceServer) ValidateState(state string) (verifier, redirectURL
 	}
 	verifier = entry.verifier
 
+	// State format: base64(redirectURL)|nonce|hmac(redirectURL|nonce)
 	parts := strings.Split(state, "|")
-	if len(parts) != 2 {
+	if len(parts) != 3 {
 		return "", "", errors.New("invalid state format")
 	}
 
 	encodedURL := parts[0]
-	providedHMAC := parts[1]
+	nonce := parts[1]
+	providedHMAC := parts[2]
 
 	redirectURLBytes, err := base64.URLEncoding.DecodeString(encodedURL)
 	if err != nil {
@@ -817,10 +830,11 @@ func (s *ProxyServiceServer) ValidateState(state string) (verifier, redirectURL
 	}
 	redirectURL = string(redirectURLBytes)
 
-	expectedHMAC := s.generateHMAC(redirectURL)
+	payload := redirectURL + "|" + nonce
+	expectedHMAC := s.generateHMAC(payload)
 
 	if !hmac.Equal([]byte(providedHMAC), []byte(expectedHMAC)) {
-		return "", "", fmt.Errorf("invalid state signature")
+		return "", "", errors.New("invalid state signature")
 	}
 
 	return verifier, redirectURL, nil
diff --git a/management/internals/shared/grpc/proxy_test.go b/management/internals/shared/grpc/proxy_test.go
index 589c57611..060af6554 100644
--- a/management/internals/shared/grpc/proxy_test.go
+++ b/management/internals/shared/grpc/proxy_test.go
@@ -1,6 +1,9 @@
 package grpc
 
 import (
+	"crypto/rand"
+	"encoding/base64"
+	"strings"
 	"sync"
 	"testing"
 	"time"
@@ -162,3 +165,68 @@ func TestSendServiceUpdate_UniqueTokensPerProxy(t *testing.T) {
 	assert.NoError(t, tokenStore.ValidateAndConsume(msg1.AuthToken, "account-1", "service-1"))
 	assert.NoError(t, tokenStore.ValidateAndConsume(msg2.AuthToken, "account-1", "service-1"))
 }
+
+// generateState creates a state using the same format as GetOIDCURL.
+func generateState(s *ProxyServiceServer, redirectURL string) string {
+	nonce := make([]byte, 16)
+	rand.Read(nonce)
+	nonceB64 := base64.URLEncoding.EncodeToString(nonce)
+
+	payload := redirectURL + "|" + nonceB64
+	hmacSum := s.generateHMAC(payload)
+	return base64.URLEncoding.EncodeToString([]byte(redirectURL)) + "|" + nonceB64 + "|" + hmacSum
+}
+
+func TestOAuthState_NeverTheSame(t *testing.T) {
+	s := &ProxyServiceServer{
+		oidcConfig: ProxyOIDCConfig{
+			HMACKey: []byte("test-hmac-key"),
+		},
+	}
+
+	redirectURL := "https://app.example.com/callback"
+
+	// Generate 100 states for the same redirect URL
+	states := make(map[string]bool)
+	for i := 0; i < 100; i++ {
+		state := generateState(s, redirectURL)
+
+		// State must have 3 parts: base64(url)|nonce|hmac
+		parts := strings.Split(state, "|")
+		require.Equal(t, 3, len(parts), "state must have 3 parts")
+
+		// State must be unique
+		require.False(t, states[state], "state %d is a duplicate", i)
+		states[state] = true
+	}
+}
+
+func TestValidateState_RejectsOldTwoPartFormat(t *testing.T) {
+	s := &ProxyServiceServer{
+		oidcConfig: ProxyOIDCConfig{
+			HMACKey: []byte("test-hmac-key"),
+		},
+	}
+
+	// Old format had only 2 parts: base64(url)|hmac
+	s.pkceVerifiers.Store("base64url|hmac", pkceEntry{verifier: "test", createdAt: time.Now()})
+
+	_, _, err := s.ValidateState("base64url|hmac")
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "invalid state format")
+}
+
+func TestValidateState_RejectsInvalidHMAC(t *testing.T) {
+	s := &ProxyServiceServer{
+		oidcConfig: ProxyOIDCConfig{
+			HMACKey: []byte("test-hmac-key"),
+		},
+	}
+
+	// Store with tampered HMAC
+	s.pkceVerifiers.Store("dGVzdA==|nonce|wrong-hmac", pkceEntry{verifier: "test", createdAt: time.Now()})
+
+	_, _, err := s.ValidateState("dGVzdA==|nonce|wrong-hmac")
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "invalid state signature")
+}