diff --git a/shortcuts/sheets/sheet_ai_api.go b/shortcuts/sheets/sheet_ai_api.go
index 0f4ee4530..da0eafa28 100644
--- a/shortcuts/sheets/sheet_ai_api.go
+++ b/shortcuts/sheets/sheet_ai_api.go
@@ -5,9 +5,12 @@ package sheets
 
 import (
 	"context"
+	"crypto/sha256"
+	"encoding/hex"
 	"encoding/json"
 	"fmt"
 	"os"
+	"strconv"
 	"strings"
 
 	"github.com/larksuite/cli/internal/output"
@@ -20,18 +23,65 @@ import (
 // transaction id for sheet tool calls.
 const sheetTxnIDEnv = "LARK_CLI_SHEET_TRANSACTION_ID"
 
-// sheetTransactionID returns the session-stable transaction id from the
-// environment, or "" when unset.
+// sheetTransactionID returns the session-stable transaction id threaded into a
+// write tool call's extra.transaction_id.
 //
 // Sheet write tools persist their reverse ("undo") changeset keyed by the
 // request's transaction id; the server mints a fresh uuid per request when the
-// caller supplies none, which isolates every CLI invocation into its own
-// single-call undo stack. Threading one stable id across a group of edits (and
-// a later +undo) is what lets +undo find and reverse those edits. An agent
-// driving lark-cli sets this once per session; empty preserves today's
-// per-request behavior.
+// caller supplies none, which would isolate every CLI invocation into its own
+// single-call undo stack. Sharing one stable id across a group of edits (and a
+// later +undo) is what lets +undo find and reverse those edits.
+//
+// Resolution order:
+//  1. $LARK_CLI_SHEET_TRANSACTION_ID — explicit caller override (highest).
+//  2. else a value derived from this shell session (see
+//     deriveSessionTransactionID) so a group of edits and a later +undo group
+//     by default, with no env var to set.
+//  3. else "" — the server mints a per-request id as before.
 func sheetTransactionID() string {
-	return strings.TrimSpace(os.Getenv(sheetTxnIDEnv))
+	if v := strings.TrimSpace(os.Getenv(sheetTxnIDEnv)); v != "" {
+		return v
+	}
+	return deriveSessionTransactionID()
+}
+
+// deriveSessionTransactionID builds a transaction id that is stable across the
+// lark-cli invocations of one shell session and distinct across sessions, so a
+// group of edits and a later +undo share an undo stack without the caller
+// exporting LARK_CLI_SHEET_TRANSACTION_ID.
+//
+// Each lark-cli run is a fresh process and cannot mutate its parent's
+// environment, so a *generated* id can't survive to the next command. Instead
+// every run independently *recomputes* the same id from its own OS session —
+// nothing is persisted between invocations.
+//
+// Returns "" when no trustworthy session signal exists (e.g. the process was
+// reparented to init); the server then mints a per-request id and a
+// missing-grouping +undo surfaces undone:0 rather than silently grouping
+// unrelated callers. The grouping signal is a per-shell-session token
+// (sessionSignal, platform-specific) salted with the uid and boot/host so a
+// session id recycled after a reboot, or reused by a different user, can't
+// collide with a stale undo stack.
+func deriveSessionTransactionID() string {
+	sig, ok := sessionSignal()
+	if !ok {
+		return ""
+	}
+	seed := strings.Join([]string{sig, strconv.Itoa(os.Getuid()), sessionSalt()}, "|")
+	sum := sha256.Sum256([]byte(seed))
+	return "larkcli-" + hex.EncodeToString(sum[:16])
+}
+
+// sessionSalt pins the derived id to this boot (Linux boot_id) or, failing
+// that, this host, so a session id recycled after a reboot can't address a
+// pre-reboot undo stack. Best-effort: an empty salt only weakens collision
+// resistance across reboots, never correctness within a session.
+func sessionSalt() string {
+	if b, err := os.ReadFile("/proc/sys/kernel/random/boot_id"); err == nil {
+		return strings.TrimSpace(string(b))
+	}
+	h, _ := os.Hostname()
+	return h
 }
 
 // ToolKind selects the One-OpenAPI endpoint and its rate-limit bucket.
diff --git a/shortcuts/sheets/sheet_ai_api_test.go b/shortcuts/sheets/sheet_ai_api_test.go
index 383d76dfb..76e13d6e2 100644
--- a/shortcuts/sheets/sheet_ai_api_test.go
+++ b/shortcuts/sheets/sheet_ai_api_test.go
@@ -3,7 +3,10 @@
 
 package sheets
 
-import "testing"
+import (
+	"strings"
+	"testing"
+)
 
 // cellsSetArgs is a minimal valid +cells-set invocation used to inspect the
 // tool-call request body.
@@ -32,13 +35,32 @@ func TestBuildToolBody_ThreadsTransactionID(t *testing.T) {
 	}
 }
 
-// TestBuildToolBody_OmitsTransactionIDWhenUnset verifies the body carries no
-// extra when the env var is empty, preserving the per-request default.
-func TestBuildToolBody_OmitsTransactionIDWhenUnset(t *testing.T) {
+// TestBuildToolBody_DerivesTransactionIDWhenUnset verifies that with the env
+// var unset a write tool carries a session-derived transaction id (so a group
+// of edits and a later +undo group by default), that the derived id is stable
+// across invocations in the same session, and that it differs from any literal
+// override. In an environment with no trustworthy session signal the derived
+// id is "" and the body carries no extra, preserving the per-request default.
+func TestBuildToolBody_DerivesTransactionIDWhenUnset(t *testing.T) {
 	t.Setenv(sheetTxnIDEnv, "")
+	want := sheetTransactionID()
 	body := parseDryRunBody(t, CellsSet, cellsSetArgs())
-	if _, ok := body["extra"]; ok {
-		t.Errorf("extra should be absent when %s is unset: %#v", sheetTxnIDEnv, body)
+	extra, hasExtra := body["extra"].(map[string]interface{})
+
+	if want == "" {
+		if hasExtra {
+			t.Errorf("no session signal: extra should be absent: %#v", body)
+		}
+		return
+	}
+	if !strings.HasPrefix(want, "larkcli-") {
+		t.Errorf("derived transaction_id = %q, want larkcli- prefix", want)
+	}
+	if !hasExtra || extra["transaction_id"] != want {
+		t.Errorf("write tool should carry derived transaction_id %q: %#v", want, body)
+	}
+	if got := sheetTransactionID(); got != want {
+		t.Errorf("derived transaction_id not stable: %q vs %q", got, want)
 	}
 }
 
diff --git a/shortcuts/sheets/sheet_session_unix.go b/shortcuts/sheets/sheet_session_unix.go
new file mode 100644
index 000000000..d4e3472e6
--- /dev/null
+++ b/shortcuts/sheets/sheet_session_unix.go
@@ -0,0 +1,32 @@
+// Copyright (c) 2026 Lark Technologies Pte. Ltd.
+// SPDX-License-Identifier: MIT
+
+//go:build !windows
+
+package sheets
+
+import (
+	"os"
+	"strconv"
+	"syscall"
+)
+
+// sessionSignal returns a token that is stable across every process of one
+// shell/login session and distinct across sessions, plus ok=false when no such
+// signal is trustworthy.
+//
+// The POSIX session id (getsid) is preferred: every process in the same
+// terminal/login session shares it, and unlike the parent pid it survives
+// subshell wrapping (e.g. `sh -c "lark-cli ..."` spawned afresh per command),
+// which is the common way an agent drives the CLI. It falls back to the parent
+// pid, then gives up when the process was reparented to init (sid/ppid <= 1) —
+// init is shared by unrelated processes and would over-group distinct callers.
+func sessionSignal() (string, bool) {
+	if sid, err := syscall.Getsid(0); err == nil && sid > 1 {
+		return "sid:" + strconv.Itoa(sid), true
+	}
+	if ppid := os.Getppid(); ppid > 1 {
+		return "ppid:" + strconv.Itoa(ppid), true
+	}
+	return "", false
+}
diff --git a/shortcuts/sheets/sheet_session_windows.go b/shortcuts/sheets/sheet_session_windows.go
new file mode 100644
index 000000000..80acb9858
--- /dev/null
+++ b/shortcuts/sheets/sheet_session_windows.go
@@ -0,0 +1,21 @@
+// Copyright (c) 2026 Lark Technologies Pte. Ltd.
+// SPDX-License-Identifier: MIT
+
+//go:build windows
+
+package sheets
+
+import (
+	"os"
+	"strconv"
+)
+
+// sessionSignal returns a per-session grouping token. Windows has no POSIX
+// session id, so the parent process id is the best portable signal; ok=false
+// when the process has no real parent (ppid <= 1).
+func sessionSignal() (string, bool) {
+	if ppid := os.Getppid(); ppid > 1 {
+		return "ppid:" + strconv.Itoa(ppid), true
+	}
+	return "", false
+}