diff --git a/apps/backend/internal/backendapp/adapters_office.go b/apps/backend/internal/backendapp/adapters_office.go
index 05e34cd8b7..4b06e421a5 100644
--- a/apps/backend/internal/backendapp/adapters_office.go
+++ b/apps/backend/internal/backendapp/adapters_office.go
@@ -230,6 +230,7 @@ func (a *configSyncerAdapter) ApplyIncoming(ctx context.Context, workspaceID str
 	return &officeonboarding.ApplyResult{
 		CreatedCount: result.CreatedCount,
 		UpdatedCount: result.UpdatedCount,
+		Warnings:     result.Warnings,
 	}, nil
 }
 
diff --git a/apps/backend/internal/office/config/dto.go b/apps/backend/internal/office/config/dto.go
index a80ac0d398..41c90b38d8 100644
--- a/apps/backend/internal/office/config/dto.go
+++ b/apps/backend/internal/office/config/dto.go
@@ -75,8 +75,9 @@ type ImportPreview struct {
 
 // ImportResult reports what was actually changed.
 type ImportResult struct {
-	CreatedCount int `json:"created_count"`
-	UpdatedCount int `json:"updated_count"`
+	CreatedCount int      `json:"created_count"`
+	UpdatedCount int      `json:"updated_count"`
+	Warnings     []string `json:"warnings,omitempty"`
 }
 
 // ParseError describes a single file that failed to parse during a FS scan.
diff --git a/apps/backend/internal/office/config/helpers_test.go b/apps/backend/internal/office/config/helpers_test.go
index 3da20cb895..209e9ca0b0 100644
--- a/apps/backend/internal/office/config/helpers_test.go
+++ b/apps/backend/internal/office/config/helpers_test.go
@@ -288,6 +288,19 @@ func fullBundle() *ConfigBundle {
 	}
 }
 
+// hierarchyAgent returns a minimal AgentConfig for reports_to resolution
+// tests. Role and counts are irrelevant to hierarchy resolution but keep the
+// fixture realistic.
+func hierarchyAgent(name, reportsTo string) AgentConfig {
+	return AgentConfig{
+		Name:                  name,
+		Role:                  "engineer",
+		ReportsTo:             reportsTo,
+		BudgetMonthlyCents:    100,
+		MaxConcurrentSessions: 1,
+	}
+}
+
 // seedAgent inserts an office agent row and returns it.
 func seedAgent(t *testing.T, e *testEnv, wsID, name string) *models.AgentInstance {
 	t.Helper()
diff --git a/apps/backend/internal/office/config/import.go b/apps/backend/internal/office/config/import.go
index 411e3fafbf..bee70a84fa 100644
--- a/apps/backend/internal/office/config/import.go
+++ b/apps/backend/internal/office/config/import.go
@@ -114,10 +114,22 @@ func (s *ConfigService) previewProjects(
 // ApplyImport applies a config bundle to the workspace, deduplicating by name.
 func (s *ConfigService) ApplyImport(
 	ctx context.Context, workspaceID string, bundle *ConfigBundle,
+) (*ImportResult, error) {
+	return s.applyImport(ctx, workspaceID, bundle, true)
+}
+
+// applyImport applies a bundle with the reports_to lookup policy for its
+// caller. Direct bundle imports may reference an existing manager that is not
+// in the bundle. Filesystem syncs are authoritative snapshots, so they must
+// resolve only against agents present in the snapshot before stale rows are
+// pruned.
+func (s *ConfigService) applyImport(
+	ctx context.Context, workspaceID string, bundle *ConfigBundle,
+	allowExternalManagers bool,
 ) (*ImportResult, error) {
 	result := &ImportResult{}
 
-	if err := s.applyAgents(ctx, workspaceID, bundle.Agents, result); err != nil {
+	if err := s.applyAgents(ctx, workspaceID, bundle.Agents, result, allowExternalManagers); err != nil {
 		return nil, fmt.Errorf("apply agents: %w", err)
 	}
 	if err := s.applySkills(ctx, workspaceID, bundle.Skills, result); err != nil {
@@ -139,6 +151,7 @@ func (s *ConfigService) ApplyImport(
 
 func (s *ConfigService) applyAgents(
 	ctx context.Context, wsID string, incoming []AgentConfig, result *ImportResult,
+	allowExternalManagers bool,
 ) error {
 	existing, err := s.repo.ListAgentInstances(ctx, wsID)
 	if err != nil {
@@ -178,9 +191,73 @@ func (s *ConfigService) applyAgents(
 			result.CreatedCount++
 		}
 	}
+	return s.applyAgentReportsTo(ctx, wsID, incoming, result, allowExternalManagers)
+}
+
+// applyAgentReportsTo resolves each incoming agent's reports_to name to the
+// target agent's ID and persists it. It runs after every agent in the bundle
+// has been created or updated above, so it re-lists the workspace to pick up
+// IDs assigned to newly-created rows — this makes resolution independent of
+// bundle order. When allowExternalManagers is true, a reports_to name may
+// also reference an agent that is only in the workspace. Filesystem syncs pass
+// false because the snapshot is authoritative and rows absent from it are
+// pruned after this import. A name that resolves to nothing (dangling
+// reference) or to the agent itself is recorded as a warning and left empty
+// rather than failing the import.
+func (s *ConfigService) applyAgentReportsTo(
+	ctx context.Context, wsID string, incoming []AgentConfig, result *ImportResult,
+	allowExternalManagers bool,
+) error {
+	current, err := s.repo.ListAgentInstances(ctx, wsID)
+	if err != nil {
+		return fmt.Errorf("resolve reports_to: list agents: %w", err)
+	}
+	byName := make(map[string]*models.AgentInstance, len(current))
+	incomingNames := bundleAgentSet(incoming)
+	for _, a := range current {
+		if !allowExternalManagers && !incomingNames[a.Name] {
+			continue
+		}
+		byName[a.Name] = a
+	}
+	for _, cfg := range incoming {
+		agent, ok := byName[cfg.Name]
+		if !ok {
+			continue
+		}
+		reportsTo, warning := resolveReportsTo(cfg, byName)
+		if warning != "" {
+			result.Warnings = append(result.Warnings, warning)
+		}
+		if agent.ReportsTo == reportsTo {
+			continue
+		}
+		agent.ReportsTo = reportsTo
+		if err := s.repo.UpdateAgentInstance(ctx, agent); err != nil {
+			return fmt.Errorf("resolve reports_to: update %q: %w", agent.Name, err)
+		}
+	}
 	return nil
 }
 
+// resolveReportsTo resolves cfg.ReportsTo (a name) against byName (a name ->
+// agent index built from the target workspace after apply). It returns the
+// resolved manager ID, or an empty string plus a warning when the name is a
+// self-reference or does not match any known agent.
+func resolveReportsTo(cfg AgentConfig, byName map[string]*models.AgentInstance) (string, string) {
+	if cfg.ReportsTo == "" {
+		return "", ""
+	}
+	if cfg.ReportsTo == cfg.Name {
+		return "", fmt.Sprintf("agent %q cannot report to itself", cfg.Name)
+	}
+	manager, ok := byName[cfg.ReportsTo]
+	if !ok {
+		return "", fmt.Sprintf("agent %q reports_to %q, which was not found", cfg.Name, cfg.ReportsTo)
+	}
+	return manager.ID, ""
+}
+
 func (s *ConfigService) applySkills(
 	ctx context.Context, wsID string, incoming []SkillConfig, result *ImportResult,
 ) error {
diff --git a/apps/backend/internal/office/config/import_reports_to_test.go b/apps/backend/internal/office/config/import_reports_to_test.go
new file mode 100644
index 0000000000..5673defb83
--- /dev/null
+++ b/apps/backend/internal/office/config/import_reports_to_test.go
@@ -0,0 +1,210 @@
+package config
+
+import (
+	"context"
+	"strings"
+	"testing"
+)
+
+// TestApplyImport_ReportsToResolvesRegardlessOfBundleOrder imports a manager
+// that appears after its report in the bundle slice and asserts resolution
+// still succeeds. The resolver re-lists agents after every create/update in
+// the bundle has run, rather than relying on encounter order.
+func TestApplyImport_ReportsToResolvesRegardlessOfBundleOrder(t *testing.T) {
+	env := newTestEnv(t)
+	ctx := context.Background()
+	bundle := &ConfigBundle{Agents: []AgentConfig{
+		hierarchyAgent("bob", "carol"),
+		hierarchyAgent("carol", ""),
+	}}
+
+	if _, err := env.svc.ApplyImport(ctx, testWorkspaceID, bundle); err != nil {
+		t.Fatalf("ApplyImport: %v", err)
+	}
+
+	carol := agentByName(t, env, testWorkspaceID, "carol")
+	bob := agentByName(t, env, testWorkspaceID, "bob")
+	assertEqual(t, "bob reports_to", bob.ReportsTo, carol.ID)
+}
+
+// TestApplyImport_ReportsToDanglingReferenceWarns asserts a reports_to naming
+// nobody leaves the field empty, does not fail the import, and records
+// exactly one warning naming both the agent and the missing manager.
+func TestApplyImport_ReportsToDanglingReferenceWarns(t *testing.T) {
+	env := newTestEnv(t)
+	ctx := context.Background()
+	bundle := &ConfigBundle{Agents: []AgentConfig{hierarchyAgent("bob", "nobody")}}
+
+	result, err := env.svc.ApplyImport(ctx, testWorkspaceID, bundle)
+	if err != nil {
+		t.Fatalf("ApplyImport: %v", err)
+	}
+	assertEqual(t, "created count", result.CreatedCount, 1)
+	assertEqual(t, "updated count", result.UpdatedCount, 0)
+	if len(result.Warnings) != 1 {
+		t.Fatalf("warnings: got %d, want 1: %v", len(result.Warnings), result.Warnings)
+	}
+	if !strings.Contains(result.Warnings[0], "bob") || !strings.Contains(result.Warnings[0], "nobody") {
+		t.Errorf("warning %q does not name both the agent and the missing manager", result.Warnings[0])
+	}
+	assertEqual(t, "bob reports_to", agentByName(t, env, testWorkspaceID, "bob").ReportsTo, "")
+}
+
+// TestApplyImport_ReportsToSelfReferenceWarns asserts an agent naming itself
+// as its own manager is skipped with a warning rather than persisted or
+// treated as an error.
+func TestApplyImport_ReportsToSelfReferenceWarns(t *testing.T) {
+	env := newTestEnv(t)
+	ctx := context.Background()
+	bundle := &ConfigBundle{Agents: []AgentConfig{hierarchyAgent("bob", "bob")}}
+
+	result, err := env.svc.ApplyImport(ctx, testWorkspaceID, bundle)
+	if err != nil {
+		t.Fatalf("ApplyImport: %v", err)
+	}
+	if len(result.Warnings) != 1 {
+		t.Fatalf("warnings: got %d, want 1: %v", len(result.Warnings), result.Warnings)
+	}
+	if !strings.Contains(result.Warnings[0], "bob") {
+		t.Errorf("warning %q does not name the self-referencing agent", result.Warnings[0])
+	}
+	assertEqual(t, "bob reports_to", agentByName(t, env, testWorkspaceID, "bob").ReportsTo, "")
+}
+
+// TestApplyImport_ReportsToIsIdempotent imports the same hierarchy bundle
+// twice and asserts the second pass leaves reports_to unchanged and does not
+// duplicate rows.
+func TestApplyImport_ReportsToIsIdempotent(t *testing.T) {
+	env := newTestEnv(t)
+	ctx := context.Background()
+	bundle := &ConfigBundle{Agents: []AgentConfig{
+		hierarchyAgent("bob", "carol"),
+		hierarchyAgent("carol", ""),
+	}}
+
+	if _, err := env.svc.ApplyImport(ctx, testWorkspaceID, bundle); err != nil {
+		t.Fatalf("first import: %v", err)
+	}
+	firstBobID := agentByName(t, env, testWorkspaceID, "bob").ID
+	firstCarolID := agentByName(t, env, testWorkspaceID, "carol").ID
+
+	if _, err := env.svc.ApplyImport(ctx, testWorkspaceID, bundle); err != nil {
+		t.Fatalf("second import: %v", err)
+	}
+
+	agents, err := env.repo.ListAgentInstances(ctx, testWorkspaceID)
+	if err != nil {
+		t.Fatalf("list agents: %v", err)
+	}
+	assertEqual(t, "agent row count", len(agents), 2)
+
+	bob := agentByName(t, env, testWorkspaceID, "bob")
+	carol := agentByName(t, env, testWorkspaceID, "carol")
+	assertEqual(t, "bob id unchanged", bob.ID, firstBobID)
+	assertEqual(t, "carol id unchanged", carol.ID, firstCarolID)
+	assertEqual(t, "bob reports_to stable", bob.ReportsTo, carol.ID)
+}
+
+// TestApplyImport_ReportsToClearsOnOmission asserts that re-importing an
+// agent with a bundle omitting reports_to clears a previously-set value,
+// matching every other field's overwrite-on-update semantics.
+func TestApplyImport_ReportsToClearsOnOmission(t *testing.T) {
+	env := newTestEnv(t)
+	ctx := context.Background()
+	seeded := &ConfigBundle{Agents: []AgentConfig{
+		hierarchyAgent("bob", "carol"),
+		hierarchyAgent("carol", ""),
+	}}
+	if _, err := env.svc.ApplyImport(ctx, testWorkspaceID, seeded); err != nil {
+		t.Fatalf("seed import: %v", err)
+	}
+	if agentByName(t, env, testWorkspaceID, "bob").ReportsTo == "" {
+		t.Fatal("setup: bob should already report to carol")
+	}
+
+	cleared := &ConfigBundle{Agents: []AgentConfig{
+		hierarchyAgent("bob", ""),
+		hierarchyAgent("carol", ""),
+	}}
+	if _, err := env.svc.ApplyImport(ctx, testWorkspaceID, cleared); err != nil {
+		t.Fatalf("clearing import: %v", err)
+	}
+	assertEqual(t, "bob reports_to cleared", agentByName(t, env, testWorkspaceID, "bob").ReportsTo, "")
+}
+
+// TestApplyImport_ReportsToRoundTripsAcrossWorkspaces exports a workspace
+// with a hierarchy and imports the resulting bundle into a separate
+// workspace (its own database, mirroring a real export/import across
+// installs), asserting the hierarchy survives the round trip.
+func TestApplyImport_ReportsToRoundTripsAcrossWorkspaces(t *testing.T) {
+	source := newTestEnv(t)
+	ctx := context.Background()
+	seeded := &ConfigBundle{Agents: []AgentConfig{
+		hierarchyAgent("bob", "carol"),
+		hierarchyAgent("carol", ""),
+	}}
+	if _, err := source.svc.ApplyImport(ctx, testWorkspaceID, seeded); err != nil {
+		t.Fatalf("seed source workspace: %v", err)
+	}
+
+	bundle, err := source.svc.ExportBundle(ctx, testWorkspaceID)
+	if err != nil {
+		t.Fatalf("ExportBundle: %v", err)
+	}
+
+	target := newTestEnv(t)
+	if _, err := target.svc.ApplyImport(ctx, testWorkspaceID, bundle); err != nil {
+		t.Fatalf("ApplyImport into target workspace: %v", err)
+	}
+
+	bob := agentByName(t, target, testWorkspaceID, "bob")
+	carol := agentByName(t, target, testWorkspaceID, "carol")
+	assertEqual(t, "bob reports_to carol in target workspace", bob.ReportsTo, carol.ID)
+}
+
+// TestApplyIncoming_PreservesReportsToFromFilesystem covers the
+// filesystem-config-sync path (ApplyIncoming -> ScanFilesystem ->
+// ApplyImport), not just the bundle-upload import endpoint. reports_to
+// written to an on-disk agent YAML file must survive the scan and resolve to
+// the manager's ID, the same as it does for a directly-uploaded bundle.
+func TestApplyIncoming_PreservesReportsToFromFilesystem(t *testing.T) {
+	env := newTestEnv(t)
+	ctx := context.Background()
+	env.writeFSAgent(t, "grace", "name: grace\nrole: manager\n")
+	env.writeFSAgent(t, "bob", "name: bob\nrole: worker\nreports_to: grace\n")
+
+	if _, err := env.svc.ApplyIncoming(ctx, testWorkspaceID); err != nil {
+		t.Fatalf("ApplyIncoming: %v", err)
+	}
+
+	grace := agentByName(t, env, testWorkspaceID, "grace")
+	bob := agentByName(t, env, testWorkspaceID, "bob")
+	assertEqual(t, "bob reports_to grace after fs sync", bob.ReportsTo, grace.ID)
+}
+
+// TestApplyIncoming_DoesNotKeepReportsToForPrunedManager verifies that the
+// incoming sync does not resolve hierarchy names against DB-only agents.
+// A manager that is absent from the filesystem must not leave a dangling ID
+// on an agent that remains in the imported bundle.
+func TestApplyIncoming_DoesNotKeepReportsToForPrunedManager(t *testing.T) {
+	env := newTestEnv(t)
+	ctx := context.Background()
+	manager := seedAgent(t, env, testWorkspaceID, "grace")
+	seedAgent(t, env, testWorkspaceID, "bob")
+	env.writeFSAgent(t, "bob", "name: bob\nrole: worker\nreports_to: grace\n")
+
+	result, err := env.svc.ApplyIncoming(ctx, testWorkspaceID)
+	if err != nil {
+		t.Fatalf("ApplyIncoming: %v", err)
+	}
+	if len(result.Warnings) != 1 {
+		t.Fatalf("warnings: got %d, want 1: %v", len(result.Warnings), result.Warnings)
+	}
+	if !strings.Contains(result.Warnings[0], "bob") || !strings.Contains(result.Warnings[0], "grace") {
+		t.Errorf("warning %q does not name both the agent and the pruned manager", result.Warnings[0])
+	}
+	assertEqual(t, "bob reports_to after manager prune", agentByName(t, env, testWorkspaceID, "bob").ReportsTo, "")
+	if _, err := env.repo.GetAgentInstance(ctx, manager.ID); err == nil {
+		t.Fatalf("pruned manager %q is still visible in the repository", manager.ID)
+	}
+}
diff --git a/apps/backend/internal/office/config/import_test.go b/apps/backend/internal/office/config/import_test.go
index 07ffe90c8e..824b5cb08b 100644
--- a/apps/backend/internal/office/config/import_test.go
+++ b/apps/backend/internal/office/config/import_test.go
@@ -57,16 +57,18 @@ func TestApplyImport_CreatesEveryFieldFromBundle(t *testing.T) {
 	assertEqual(t, "project executor config", project.ExecutorConfig, `{"type":"local_docker"}`)
 }
 
-// TestApplyImport_NameReferencesAreNotResolved pins the deliberate gap in the
-// importer: the three cross-entity references in the DTO (agent reports_to,
-// routine assignee_name, project lead_agent_name) name an entity but the
-// import never resolves them to an ID. They are export-only fields today.
-// Wiring resolution in must update this test.
+// TestApplyImport_NameReferencesAreNotResolved documents the current state of
+// the three cross-entity references in the DTO (agent reports_to, routine
+// assignee_name, project lead_agent_name): agent reports_to IS resolved to
+// the target agent's ID (see the reports_to-specific tests in
+// import_reports_to_test.go for the full behavior), but routine assignee_name
+// and project lead_agent_name remain export-only fields that import never
+// resolves. Wiring resolution in for those must update this test.
 func TestApplyImport_NameReferencesAreNotResolved(t *testing.T) {
 	env := newTestEnv(t)
 	ctx := context.Background()
 
-	// Seed the referenced agent so a resolver would have something to find.
+	// Seed the referenced agent so the resolver has something to find.
 	lead := seedAgent(t, env, testWorkspaceID, "grace")
 
 	if _, err := env.svc.ApplyImport(ctx, testWorkspaceID, fullBundle()); err != nil {
@@ -74,10 +76,7 @@ func TestApplyImport_NameReferencesAreNotResolved(t *testing.T) {
 	}
 
 	agent := agentByName(t, env, testWorkspaceID, "ada")
-	assertEqual(t, "agent reports_to", agent.ReportsTo, "")
-	if agent.ReportsTo == lead.ID {
-		t.Error("reports_to resolution appears implemented; update this test")
-	}
+	assertEqual(t, "agent reports_to", agent.ReportsTo, lead.ID)
 	assertEqual(t, "routine assignee",
 		routineByName(t, env, testWorkspaceID, "standup").AssigneeAgentProfileID, "")
 	assertEqual(t, "project lead",
diff --git a/apps/backend/internal/office/config/sync.go b/apps/backend/internal/office/config/sync.go
index 7911d5214a..8980338168 100644
--- a/apps/backend/internal/office/config/sync.go
+++ b/apps/backend/internal/office/config/sync.go
@@ -19,7 +19,7 @@ func (s *ConfigService) ScanFilesystem(_ context.Context, _ string) (*ConfigBund
 	bundle := &ConfigBundle{Settings: SettingsConfig{Name: defaultWorkspaceName}}
 	for _, a := range s.cfgLoader.GetAgents(defaultWorkspaceName) {
 		bundle.Agents = append(bundle.Agents, AgentConfig{
-			Name: a.Name, Role: string(a.Role), Icon: a.Icon,
+			Name: a.Name, Role: string(a.Role), Icon: a.Icon, ReportsTo: a.ReportsTo,
 			BudgetMonthlyCents: a.BudgetMonthlyCents, MaxConcurrentSessions: a.MaxConcurrentSessions,
 			DesiredSkills: a.DesiredSkills, ExecutorPreference: a.ExecutorPreference,
 		})
@@ -97,7 +97,9 @@ func (s *ConfigService) ApplyIncoming(ctx context.Context, workspaceID string) (
 	if err != nil {
 		return nil, err
 	}
-	result, err := s.ApplyImport(ctx, workspaceID, bundle)
+	// The filesystem is an authoritative snapshot for this direction. Do not
+	// resolve reports_to against DB-only managers because they are pruned below.
+	result, err := s.applyImport(ctx, workspaceID, bundle, false)
 	if err != nil {
 		return nil, err
 	}
diff --git a/apps/backend/internal/office/config/sync_test.go b/apps/backend/internal/office/config/sync_test.go
index a31e92e955..233fb29dc4 100644
--- a/apps/backend/internal/office/config/sync_test.go
+++ b/apps/backend/internal/office/config/sync_test.go
@@ -81,6 +81,7 @@ func TestScanFilesystem_CarriesEveryFieldFromDisk(t *testing.T) {
 	assertEqual(t, "agent name", agent.Name, "ada")
 	assertEqual(t, "agent role", agent.Role, "cto")
 	assertEqual(t, "agent icon", agent.Icon, "🤖")
+	assertEqual(t, "agent reports_to", agent.ReportsTo, "grace")
 	assertEqual(t, "agent budget", agent.BudgetMonthlyCents, 4200)
 	assertEqual(t, "agent max sessions", agent.MaxConcurrentSessions, 3)
 	assertEqual(t, "agent desired skills", agent.DesiredSkills, `["go","sql"]`)
@@ -117,15 +118,16 @@ func TestScanFilesystem_CarriesEveryFieldFromDisk(t *testing.T) {
 		`{"type":"local_docker"}`)
 }
 
-// TestScanFilesystem_DropsNameReferences records the same gap the importer
-// has: the scan does not carry reports_to, assignee_name or lead_agent_name
-// off disk even though all three are present in the fixture files. The result
-// is a lossy sync — applying a checked-in workspace config erases the org
-// chart, routine assignees and project leads rather than resolving the
-// portable names to IDs.
+// TestScanFilesystem_DropsNameReferences records a gap that remains for
+// routines and projects: the scan does not carry assignee_name or
+// lead_agent_name off disk even though both are present in the fixture
+// files. The result is a lossy sync for those two fields — applying a
+// checked-in workspace config erases routine assignees and project leads
+// rather than resolving the portable names to IDs. Agent reports_to no
+// longer drops (see TestScanFilesystem_CarriesEveryFieldFromDisk).
 //
-// Recorded rather than fixed (test-only change); carrying the names through
-// the scan and resolving them on import must update this test.
+// Recorded rather than fixed (test-only change); carrying the remaining
+// names through the scan and resolving them on import must update this test.
 func TestScanFilesystem_DropsNameReferences(t *testing.T) {
 	env := newTestEnv(t)
 	seedFullFSState(t, env)
@@ -134,7 +136,6 @@ func TestScanFilesystem_DropsNameReferences(t *testing.T) {
 	if err != nil {
 		t.Fatalf("ScanFilesystem: %v", err)
 	}
-	assertEqual(t, "agent reports_to", bundle.Agents[0].ReportsTo, "")
 	assertEqual(t, "routine assignee", bundle.Routines[0].AssigneeName, "")
 	assertEqual(t, "project lead", bundle.Projects[0].LeadAgentName, "")
 }
diff --git a/apps/backend/internal/office/config/sync_util.go b/apps/backend/internal/office/config/sync_util.go
index 804fc326d7..41fb15a105 100644
--- a/apps/backend/internal/office/config/sync_util.go
+++ b/apps/backend/internal/office/config/sync_util.go
@@ -126,6 +126,7 @@ func writeBundleEntities(w *configloader.FileWriter, bundle *ConfigBundle) error
 	for _, a := range bundle.Agents {
 		agent := &models.AgentInstance{
 			Name: a.Name, Role: models.AgentRole(a.Role), Icon: a.Icon,
+			ReportsTo:          a.ReportsTo,
 			BudgetMonthlyCents: a.BudgetMonthlyCents, MaxConcurrentSessions: a.MaxConcurrentSessions,
 			DesiredSkills: a.DesiredSkills, ExecutorPreference: a.ExecutorPreference,
 		}
diff --git a/apps/backend/internal/office/config/sync_util_test.go b/apps/backend/internal/office/config/sync_util_test.go
index d7ad4e5db8..461873ed36 100644
--- a/apps/backend/internal/office/config/sync_util_test.go
+++ b/apps/backend/internal/office/config/sync_util_test.go
@@ -143,6 +143,7 @@ func TestWriteBundleToFS_AllFieldsReachDisk(t *testing.T) {
 	assertEqual(t, "agent name", got.Name, "ada")
 	assertEqual(t, "agent role", string(got.Role), "cto")
 	assertEqual(t, "agent icon", got.Icon, "🤖")
+	assertEqual(t, "agent reports_to", got.ReportsTo, "grace")
 	assertEqual(t, "agent budget", got.BudgetMonthlyCents, 4200)
 	assertEqual(t, "agent max sessions", got.MaxConcurrentSessions, 3)
 	assertEqual(t, "agent desired skills", got.DesiredSkills, `["go","sql"]`)
diff --git a/apps/backend/internal/office/onboarding/dto.go b/apps/backend/internal/office/onboarding/dto.go
index 5e5380d5c9..1b0fefbb26 100644
--- a/apps/backend/internal/office/onboarding/dto.go
+++ b/apps/backend/internal/office/onboarding/dto.go
@@ -18,6 +18,7 @@ type OnboardingStateResponse struct {
 type OnboardingImportFSResponse struct {
 	WorkspaceIDs  []string `json:"workspaceIds"`
 	ImportedCount int      `json:"importedCount"`
+	Warnings      []string `json:"warnings,omitempty"`
 }
 
 // OnboardingCompleteRequest is the request body for POST /onboarding/complete.
diff --git a/apps/backend/internal/office/onboarding/handler.go b/apps/backend/internal/office/onboarding/handler.go
index 27a79bceb4..816d88d9f2 100644
--- a/apps/backend/internal/office/onboarding/handler.go
+++ b/apps/backend/internal/office/onboarding/handler.go
@@ -91,5 +91,6 @@ func (h *Handler) importFromFS(c *gin.Context) {
 	c.JSON(http.StatusOK, OnboardingImportFSResponse{
 		WorkspaceIDs:  result.WorkspaceIDs,
 		ImportedCount: result.ImportedCount,
+		Warnings:      result.Warnings,
 	})
 }
diff --git a/apps/backend/internal/office/onboarding/service.go b/apps/backend/internal/office/onboarding/service.go
index a085fc92e0..88ca65afbf 100644
--- a/apps/backend/internal/office/onboarding/service.go
+++ b/apps/backend/internal/office/onboarding/service.go
@@ -102,6 +102,7 @@ type ConfigSyncer interface {
 type ApplyResult struct {
 	CreatedCount int
 	UpdatedCount int
+	Warnings     []string
 }
 
 // RunReason for a newly assigned task.
@@ -211,6 +212,7 @@ type CompleteResult struct {
 type ImportFromFSResult struct {
 	WorkspaceIDs  []string
 	ImportedCount int
+	Warnings      []string
 }
 
 // GetOnboardingState checks whether onboarding has been completed.
@@ -440,6 +442,7 @@ func (s *OnboardingService) importSingleWorkspace(
 			return "", false
 		}
 		result.ImportedCount += importResult.CreatedCount + importResult.UpdatedCount
+		result.Warnings = append(result.Warnings, importResult.Warnings...)
 	}
 	return wsID, true
 }
diff --git a/apps/backend/internal/office/onboarding/service_test.go b/apps/backend/internal/office/onboarding/service_test.go
index e138fbf3c0..7e55cec3cc 100644
--- a/apps/backend/internal/office/onboarding/service_test.go
+++ b/apps/backend/internal/office/onboarding/service_test.go
@@ -84,6 +84,14 @@ type mockWorkflowEnsurer struct {
 	defaultID string
 }
 
+type mockConfigSyncer struct {
+	result *ApplyResult
+}
+
+func (m *mockConfigSyncer) ApplyIncoming(_ context.Context, _ string) (*ApplyResult, error) {
+	return m.result, nil
+}
+
 func (m *mockWorkflowEnsurer) EnsureOfficeWorkflow(_ context.Context, _ string) (string, error) {
 	return m.officeID, nil
 }
@@ -575,6 +583,29 @@ func TestImportFromFS_SkipsAlreadyImported(t *testing.T) {
 	}
 }
 
+func TestImportFromFS_PropagatesSyncWarnings(t *testing.T) {
+	svc, _, _ := newTestOnboardingService(t)
+	svc.configSyncer = &mockConfigSyncer{result: &ApplyResult{
+		CreatedCount: 2,
+		UpdatedCount: 1,
+		Warnings:     []string{"agent \"bob\" reports_to \"grace\", which was not found"},
+	}}
+
+	result, err := svc.ImportFromFS(context.Background())
+	if err != nil {
+		t.Fatalf("import from fs: %v", err)
+	}
+	if result.ImportedCount != 3 {
+		t.Fatalf("imported count: got %d, want 3", result.ImportedCount)
+	}
+	if len(result.Warnings) != 1 {
+		t.Fatalf("warnings: got %d, want 1: %v", len(result.Warnings), result.Warnings)
+	}
+	if result.Warnings[0] != "agent \"bob\" reports_to \"grace\", which was not found" {
+		t.Errorf("warning: got %q", result.Warnings[0])
+	}
+}
+
 // onboardingRoutingScenario is one row in the default-tier seeding
 // table. It captures the wizard's tier input plus the expected
 // outcome on the persisted office_workspace_routing row.
diff --git a/apps/web/app/office/setup/setup-wizard.tsx b/apps/web/app/office/setup/setup-wizard.tsx
index 49c2b9d075..d9fb6857a4 100644
--- a/apps/web/app/office/setup/setup-wizard.tsx
+++ b/apps/web/app/office/setup/setup-wizard.tsx
@@ -233,6 +233,9 @@ export function SetupWizard({
     try {
       const result = await importFromFS();
       toast.success(t("office:importedConfigEntries", { importedCount: result.importedCount }));
+      if (result.warnings?.length) {
+        toast.warning(result.warnings.join("\n"));
+      }
       router.push("/office");
       router.refresh();
     } catch (err) {
diff --git a/apps/web/app/office/workspace/settings/sync/use-sync-state.ts b/apps/web/app/office/workspace/settings/sync/use-sync-state.ts
index 7e3d9bcf4b..af4ce0e317 100644
--- a/apps/web/app/office/workspace/settings/sync/use-sync-state.ts
+++ b/apps/web/app/office/workspace/settings/sync/use-sync-state.ts
@@ -51,6 +51,9 @@ export function useSyncState(activeWorkspaceId: string) {
           updated: res.result.updated_count,
         }),
       );
+      if (res.result.warnings?.length) {
+        toast.warning(res.result.warnings.join("\n"));
+      }
       await refresh();
     } catch (err) {
       toast.error(err instanceof Error ? err.message : t(MSG_IMPORT_FAIL));
diff --git a/apps/web/lib/api/domains/office-extended-api.ts b/apps/web/lib/api/domains/office-extended-api.ts
index ff899726d4..4b80625980 100644
--- a/apps/web/lib/api/domains/office-extended-api.ts
+++ b/apps/web/lib/api/domains/office-extended-api.ts
@@ -80,13 +80,12 @@ export function applyImport(
   bundle: Record<string, unknown>,
   options?: ApiRequestOptions,
 ) {
-  return fetchJson<{ result: { created_count: number; updated_count: number } }>(
-    `${BASE}/workspaces/${workspaceId}/config/import`,
-    {
-      ...options,
-      init: { method: "POST", body: JSON.stringify(bundle), ...options?.init },
-    },
-  );
+  return fetchJson<{
+    result: { created_count: number; updated_count: number; warnings?: string[] };
+  }>(`${BASE}/workspaces/${workspaceId}/config/import`, {
+    ...options,
+    init: { method: "POST", body: JSON.stringify(bundle), ...options?.init },
+  });
 }
 
 // --- Config Sync (FS <-> DB) ---
@@ -131,10 +130,12 @@ export function getOutgoingDiff(workspaceId: string, options?: ApiRequestOptions
 }
 
 export function applyIncomingSync(workspaceId: string, options?: ApiRequestOptions) {
-  return fetchJson<{ result: { created_count: number; updated_count: number } }>(
-    `${BASE}/workspaces/${workspaceId}/config/sync/import-fs`,
-    { ...options, init: { method: "POST", ...options?.init } },
-  );
+  return fetchJson<{
+    result: { created_count: number; updated_count: number; warnings?: string[] };
+  }>(`${BASE}/workspaces/${workspaceId}/config/sync/import-fs`, {
+    ...options,
+    init: { method: "POST", ...options?.init },
+  });
 }
 
 export function applyOutgoingSync(workspaceId: string, options?: ApiRequestOptions) {
@@ -493,6 +494,7 @@ export function completeOnboarding(data: OnboardingCompletePayload, options?: Ap
 export type ImportFromFSResult = {
   workspaceIds: string[];
   importedCount: number;
+  warnings?: string[];
 };
 
 export function importFromFS(options?: ApiRequestOptions) {