diff --git a/workspace-server/internal/handlers/org_import.go b/workspace-server/internal/handlers/org_import.go
index 49dc64fbc..970aa702b 100644
--- a/workspace-server/internal/handlers/org_import.go
+++ b/workspace-server/internal/handlers/org_import.go
@@ -548,6 +548,16 @@ func (h *OrgHandler) createWorkspaceTree(ws OrgWorkspace, parentID *string, absX
 		})
 	}
 
+	// internal#2006: migrate runtime-created schedules from a removed
+	// predecessor of the same agent (role+parent) onto this freshly-created
+	// workspace. Reconcile re-derives template-sourced state below, but
+	// schedules a user added at runtime (source='runtime', via the canvas/API)
+	// bind to the ephemeral workspace_id and would otherwise be abandoned on
+	// the removed row when an agent is recreated with a new id. Runs before the
+	// template upsert loop so a same-named template schedule still wins.
+	// Best-effort: never fails the import.
+	h.migrateRuntimeSchedulesFromRemovedPredecessor(ctx, id, role, ws.Name, parentID)
+
 	// Insert schedules if defined. Resolve each schedule's prompt body from
 	// either inline `prompt:` or `prompt_file:` (file ref relative to the
 	// workspace's files_dir). Inline wins; empty prompt after resolution is
@@ -687,6 +697,64 @@ func (h *OrgHandler) createWorkspaceTree(ws OrgWorkspace, parentID *string, absX
 	return h.recurseChildrenForImport(ws, id, absX, absY, defaults, orgBaseDir, results, provisionSem)
 }
 
+// migrateRuntimeSchedulesFromRemovedPredecessor re-points runtime-created
+// schedules (source='runtime') from the most-recent removed predecessor of the
+// same agent onto newID. Recreating an agent mints a NEW workspace id (the
+// ON CONFLICT in createWorkspaceTree only matches non-removed rows), so a
+// schedule a user added at runtime would otherwise be abandoned on the removed
+// row. Template-sourced schedules are NOT migrated — reconcile re-derives those
+// from the org template (the upsert loop). The predecessor is matched by the
+// stable `role` when present (survives the name auto-suffixing that yields
+// "Agent (2)"), falling back to name+parent. Idempotent (skips names already on
+// newID) and best-effort (logs, never errors the import). See internal#2006.
+func (h *OrgHandler) migrateRuntimeSchedulesFromRemovedPredecessor(ctx context.Context, newID string, role interface{}, name string, parentID *string) {
+	var predID string
+	var err error
+	if role != nil {
+		err = db.DB.QueryRowContext(ctx, `
+			SELECT id FROM workspaces
+			WHERE status = 'removed' AND role = $1
+			  AND parent_id IS NOT DISTINCT FROM $2
+			  AND id <> $3
+			ORDER BY updated_at DESC NULLS LAST
+			LIMIT 1
+		`, role, parentID, newID).Scan(&predID)
+	} else {
+		err = db.DB.QueryRowContext(ctx, `
+			SELECT id FROM workspaces
+			WHERE status = 'removed' AND name = $1
+			  AND parent_id IS NOT DISTINCT FROM $2
+			  AND id <> $3
+			ORDER BY updated_at DESC NULLS LAST
+			LIMIT 1
+		`, name, parentID, newID).Scan(&predID)
+	}
+	if errors.Is(err, sql.ErrNoRows) {
+		return // first-time create — no predecessor to migrate from
+	}
+	if err != nil {
+		log.Printf("Org import: predecessor lookup for %q (new=%s) failed: %v — skipping schedule migration", name, newID, err)
+		return
+	}
+	res, err := db.DB.ExecContext(ctx, `
+		UPDATE workspace_schedules s
+		SET workspace_id = $1, updated_at = now()
+		WHERE s.workspace_id = $2
+		  AND s.source = 'runtime'
+		  AND NOT EXISTS (
+		      SELECT 1 FROM workspace_schedules t
+		      WHERE t.workspace_id = $1 AND t.name = s.name
+		  )
+	`, newID, predID)
+	if err != nil {
+		log.Printf("Org import: schedule migration %s -> %s (%q) failed: %v", predID, newID, name, err)
+		return
+	}
+	if n, _ := res.RowsAffected(); n > 0 {
+		log.Printf("Org import: migrated %d runtime schedule(s) from removed predecessor %s to new workspace %s (%q)", n, predID, newID, name)
+	}
+}
+
 // lookupExistingChild returns the id of an existing workspace under
 // (parent_id, name) if any, with idempotency-friendly semantics:
 //   - parent_id IS NOT DISTINCT FROM matches NULL too (root workspaces)
diff --git a/workspace-server/internal/handlers/org_import_schedule_migration_test.go b/workspace-server/internal/handlers/org_import_schedule_migration_test.go
new file mode 100644
index 000000000..72e6a5f87
--- /dev/null
+++ b/workspace-server/internal/handlers/org_import_schedule_migration_test.go
@@ -0,0 +1,75 @@
+package handlers
+
+import (
+	"context"
+	"database/sql"
+	"testing"
+
+	sqlmock "github.com/DATA-DOG/go-sqlmock"
+)
+
+// TestMigrateRuntimeSchedulesFromRemovedPredecessor verifies the happy path:
+// a removed predecessor exists for the agent (matched by role), and its
+// runtime-created schedules are re-pointed onto the freshly-created workspace.
+// internal#2006 (recreate-orphans-schedules regression).
+func TestMigrateRuntimeSchedulesFromRemovedPredecessor(t *testing.T) {
+	mock := setupTestDB(t)
+	h := &OrgHandler{}
+
+	// Predecessor lookup (role branch) returns the removed prior workspace.
+	mock.ExpectQuery(`SELECT id FROM workspaces`).
+		WillReturnRows(sqlmock.NewRows([]string{"id"}).AddRow("old-removed-ws"))
+	// Re-point UPDATE migrates 2 runtime schedules.
+	mock.ExpectExec(`UPDATE workspace_schedules`).
+		WillReturnResult(sqlmock.NewResult(0, 2))
+
+	parent := "parent-1"
+	h.migrateRuntimeSchedulesFromRemovedPredecessor(
+		context.Background(), "new-ws", interface{}("code-reviewer"), "Code Reviewer (2)", &parent,
+	)
+
+	if err := mock.ExpectationsWereMet(); err != nil {
+		t.Fatalf("unmet sqlmock expectations: %v", err)
+	}
+}
+
+// TestMigrateRuntimeSchedules_NoPredecessor verifies the first-time-create path:
+// no removed predecessor → the function returns after the lookup and MUST NOT
+// run the re-point UPDATE (sqlmock errors on an unexpected query if it does).
+func TestMigrateRuntimeSchedules_NoPredecessor(t *testing.T) {
+	mock := setupTestDB(t)
+	h := &OrgHandler{}
+
+	mock.ExpectQuery(`SELECT id FROM workspaces`).
+		WillReturnError(sql.ErrNoRows)
+	// No ExpectExec — an UPDATE here would be an unexpected query → test fails.
+
+	h.migrateRuntimeSchedulesFromRemovedPredecessor(
+		context.Background(), "new-ws", interface{}("researcher"), "Root-Cause Researcher", nil,
+	)
+
+	if err := mock.ExpectationsWereMet(); err != nil {
+		t.Fatalf("unmet sqlmock expectations: %v", err)
+	}
+}
+
+// TestMigrateRuntimeSchedules_NameFallback verifies the name-branch lookup is
+// used when the agent has no stable role (role == nil), still followed by the
+// re-point UPDATE.
+func TestMigrateRuntimeSchedules_NameFallback(t *testing.T) {
+	mock := setupTestDB(t)
+	h := &OrgHandler{}
+
+	mock.ExpectQuery(`SELECT id FROM workspaces`).
+		WillReturnRows(sqlmock.NewRows([]string{"id"}).AddRow("old-removed-ws"))
+	mock.ExpectExec(`UPDATE workspace_schedules`).
+		WillReturnResult(sqlmock.NewResult(0, 1))
+
+	h.migrateRuntimeSchedulesFromRemovedPredecessor(
+		context.Background(), "new-ws", nil, "Some Agent", nil,
+	)
+
+	if err := mock.ExpectationsWereMet(); err != nil {
+		t.Fatalf("unmet sqlmock expectations: %v", err)
+	}
+}