diff --git a/internal/imclient/client.go b/internal/imclient/client.go
index 9617ac9..0366a64 100644
--- a/internal/imclient/client.go
+++ b/internal/imclient/client.go
@@ -388,6 +388,12 @@ func IsConflict(err error) bool {
 	return errors.As(err, &target) && target.Status == http.StatusConflict
 }
 
+func IsFriendRequestConflict(err error) bool {
+	var target *Error
+	return errors.As(err, &target) && target.Status == http.StatusConflict &&
+		strings.EqualFold(strings.TrimSpace(target.Reason), "FRIEND_REQUEST_CONFLICT")
+}
+
 func IsPermissionDenied(err error) bool {
 	var target *Error
 	return errors.As(err, &target) && target.Status == http.StatusForbidden
diff --git a/internal/support/service.go b/internal/support/service.go
index 97081ae..bdaf1f9 100644
--- a/internal/support/service.go
+++ b/internal/support/service.go
@@ -125,42 +125,42 @@ func (s *Service) OpenSession(ctx context.Context, tenantID, memberID, serviceID
 	if !strings.EqualFold(strings.TrimSpace(imSession.UserID), strings.TrimSpace(identity.IMUserID)) {
 		return nil, ErrIMUnavailable
 	}
-	var conversation *imclient.Conversation
 	profile, err := s.im.UserProfile(ctx, imSession.Token, agent.IMUserID)
+	relationship := ""
 	if err != nil {
 		if !imclient.IsPermissionDenied(err) {
 			return nil, fmt.Errorf("query customer service relationship: %w", err)
 		}
-		conversation, err = s.im.EnsureP2P(ctx, imSession.Token, agent.IMUserID,
-			fmt.Sprintf("p2p:%s:%s", identity.IMUserID, agent.IMUserID))
-		if err != nil {
-			return nil, fmt.Errorf("query customer service relationship: %w", err)
+		key := fmt.Sprintf("customer-service:%d:%d:%d", tenantID, memberID, serviceID)
+		request, requestErr := s.im.CreateFriendRequest(ctx, imSession.Token, agent.IMUserID, key)
+		if imclient.IsFriendRequestConflict(requestErr) {
+			return nil, ErrRelationPending
 		}
-	}
-	relationship := ""
-	if profile != nil {
-		relationship = strings.TrimSpace(profile.Relationship)
+		if requestErr != nil {
+			if imclient.IsConflict(requestErr) {
+				return nil, ErrRelationDenied
+			}
+			return nil, fmt.Errorf("create customer service friend request: %w", requestErr)
+		}
+		relationship = strings.TrimSpace(request.Status)
 	} else {
-		relationship = strings.TrimSpace(conversation.Relationship)
+		relationship = strings.TrimSpace(profile.Relationship)
 	}
 	switch relationship {
 	case "friend":
 	case "none", "":
 		key := fmt.Sprintf("customer-service:%d:%d:%d", tenantID, memberID, serviceID)
 		request, requestErr := s.im.CreateFriendRequest(ctx, imSession.Token, agent.IMUserID, key)
+		if imclient.IsFriendRequestConflict(requestErr) {
+			return nil, ErrRelationPending
+		}
 		if requestErr != nil && !imclient.IsConflict(requestErr) {
 			return nil, fmt.Errorf("create customer service friend request: %w", requestErr)
 		}
 		if requestErr != nil {
-			conversation, err = s.im.EnsureP2P(ctx, imSession.Token, agent.IMUserID,
-				fmt.Sprintf("p2p:%s:%s", identity.IMUserID, agent.IMUserID))
-			if err != nil {
-				return nil, fmt.Errorf("refresh customer service relationship: %w", err)
-			}
-			relationship = strings.TrimSpace(conversation.Relationship)
+			return nil, ErrRelationDenied
 		} else {
 			relationship = strings.TrimSpace(request.Status)
-			conversation = nil
 		}
 		if relationship != "accepted" && relationship != "friend" {
 			return nil, ErrRelationPending
@@ -170,12 +170,10 @@ func (s *Service) OpenSession(ctx context.Context, tenantID, memberID, serviceID
 	default:
 		return nil, ErrRelationDenied
 	}
-	if conversation == nil {
-		conversation, err = s.im.EnsureP2P(ctx, imSession.Token, agent.IMUserID,
-			fmt.Sprintf("p2p:%s:%s", identity.IMUserID, agent.IMUserID))
-		if err != nil {
-			return nil, fmt.Errorf("ensure customer service conversation: %w", err)
-		}
+	conversation, err := s.im.EnsureP2P(ctx, imSession.Token, agent.IMUserID,
+		fmt.Sprintf("p2p:%s:%s", identity.IMUserID, agent.IMUserID))
+	if err != nil {
+		return nil, fmt.Errorf("ensure customer service conversation: %w", err)
 	}
 	if strings.TrimSpace(conversation.Topic) == "" || (conversation.Relationship != "" && conversation.Relationship != "friend") || !conversation.CanSend {
 		return nil, ErrRelationDenied
diff --git a/internal/support/service_test.go b/internal/support/service_test.go
index 9c36dee..78831af 100644
--- a/internal/support/service_test.go
+++ b/internal/support/service_test.go
@@ -37,13 +37,15 @@ func (r *repositoryStub) SaveMemberIMIdentity(_ context.Context, identity *store
 }
 
 type imStub struct {
-	friendRequests int
-	loginAttempts  int
-	resetPasswords int
-	loginError     error
-	profileError   error
-	conversation   *imclient.Conversation
-	ensureP2PCalls int
+	friendRequests  int
+	loginAttempts   int
+	resetPasswords  int
+	loginError      error
+	profileError    error
+	friendError     error
+	conversation    *imclient.Conversation
+	conversationErr error
+	ensureP2PCalls  int
 }
 
 func (i *imStub) Ready() bool { return true }
@@ -78,10 +80,16 @@ func (i *imStub) UserProfile(context.Context, string, string) (*imclient.UserPro
 }
 func (i *imStub) CreateFriendRequest(context.Context, string, string, string) (*imclient.FriendRequest, error) {
 	i.friendRequests++
+	if i.friendError != nil {
+		return nil, i.friendError
+	}
 	return &imclient.FriendRequest{RequestID: "frq_1", Status: "accepted"}, nil
 }
 func (i *imStub) EnsureP2P(context.Context, string, string, string) (*imclient.Conversation, error) {
 	i.ensureP2PCalls++
+	if i.conversationErr != nil {
+		return nil, i.conversationErr
+	}
 	if i.conversation != nil {
 		return i.conversation, nil
 	}
@@ -132,8 +140,9 @@ func TestOpenSessionReturnsPendingWhenPrivateProfileHidesPendingRelationship(t *
 		identity: &store.MemberIMIdentity{TenantID: 0, MemberID: 9, IMTenantCode: "allrich", IMUserID: "usr_member", IMUsername: "member01"},
 	}
 	im := &imStub{
-		profileError: &imclient.Error{Status: 403, Reason: "PERMISSION_DENIED"},
-		conversation: &imclient.Conversation{Topic: "p2p-topic", Relationship: "pending_outbound", CanSend: false},
+		profileError:    &imclient.Error{Status: 403, Reason: "PERMISSION_DENIED"},
+		friendError:     &imclient.Error{Status: 409, Reason: "FRIEND_REQUEST_CONFLICT"},
+		conversationErr: &imclient.Error{Status: 403, Reason: "PERMISSION_DENIED"},
 	}
 	service := New(repository, im, config.AuthConfig{FinanceMasterKey: strings.Repeat("k", 32)})
 	repository.identity.IMPasswordCipher, _ = service.encryptCredential("password")
@@ -142,8 +151,8 @@ func TestOpenSessionReturnsPendingWhenPrivateProfileHidesPendingRelationship(t *
 	if !errors.Is(err, ErrRelationPending) {
 		t.Fatalf("error = %v, want ErrRelationPending", err)
 	}
-	if im.ensureP2PCalls != 1 || im.friendRequests != 0 {
-		t.Fatalf("ensure p2p calls=%d friend requests=%d, want 1 and 0", im.ensureP2PCalls, im.friendRequests)
+	if im.ensureP2PCalls != 0 || im.friendRequests != 1 {
+		t.Fatalf("ensure p2p calls=%d friend requests=%d, want 0 and 1", im.ensureP2PCalls, im.friendRequests)
 	}
 }