diff --git a/README.md b/README.md
index bcf0d9a..780269d 100644
--- a/README.md
+++ b/README.md
@@ -48,7 +48,7 @@ All subcommands accept these persistent flags:
 - `renamer replace <pattern...> <replacement>` — Replace multiple literal tokens in sequence. Shows duplicates and conflict warnings, then applies when `--yes` is present.
 - `renamer remove <pattern...>` — Strip ordered substrings from names with empty-name protection and duplicate detection.
 - `renamer extension <source-ext...> <target-ext>` — Normalize heterogeneous extensions to a single target while keeping a ledger entry for undo.
-- `renamer insert <position> <text>` — Insert text at symbolic (`^`, `$`) or numeric offsets (positive or negative).
+- `renamer insert <position> <text>` — Insert text at symbolic (`^`, `$`) offsets, count forward with numbers (`3` or `^3`), or backward with suffix tokens like `1$`.
 - `renamer regex <pattern> <template>` — Rename via RE2 capture groups using placeholders like `@1`, `@2`, `@0`, or escape literal `@` as `@@`.
 - `renamer undo` — Revert the most recent mutating command recorded in the ledger.
 
diff --git a/cmd/insert.go b/cmd/insert.go
index 69497ed..ef5456e 100644
--- a/cmd/insert.go
+++ b/cmd/insert.go
@@ -17,7 +17,7 @@ func newInsertCommand() *cobra.Command {
 		Short: "Insert text into filenames at specified positions",
 		Long: `Insert a Unicode string into each candidate filename at a specific position.
 Supported positions: "^" (start), "$" (before extension), positive indexes (1-based),
-negative indexes counting back from the end.`,
+and suffix offsets like "3$" counting backward from the end.`,
 		Args: cobra.MinimumNArgs(2),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			scope, err := listing.ScopeFromCmd(cmd)
@@ -80,7 +80,7 @@ negative indexes counting back from the end.`,
 	}
 
 	cmd.Example = `  renamer insert ^ "[2025] " --dry-run
-  renamer insert -1 _FINAL --yes --path ./reports`
+  renamer insert 1$ _FINAL --yes --path ./reports`
 
 	return cmd
 }
diff --git a/docs/cli-flags.md b/docs/cli-flags.md
index 788a8b5..e52c91a 100644
--- a/docs/cli-flags.md
+++ b/docs/cli-flags.md
@@ -39,10 +39,8 @@ renamer insert <position> <text> [flags]
 ```
 
 - Position tokens:
-  - `^` inserts at the beginning of the filename.
-  - `$` inserts immediately before the extension dot (or end if no extension).
-  - Positive integers (1-based) count forward from the start of the stem.
-  - Negative integers count backward from the end of the stem (e.g., `-1` inserts before the last rune).
+  - `^` inserts at the beginning of the filename. Append a number (`^3` or just `3`) to insert after the third rune of the stem.
+  - `$` inserts immediately before the extension dot (or end if no extension). Append a number (`1$`) to count backward from the end of the stem (e.g., `1$` inserts before the final rune).
 - Text must be valid UTF-8 without path separators or control characters; Unicode characters are supported.
 - Scope flags (`--path`, `-r`, `-d`, `--hidden`, `--extensions`) limit the candidate set before insertion.
 - `--dry-run` previews the plan; rerun with `--yes` to apply the same operations.
@@ -51,6 +49,7 @@ renamer insert <position> <text> [flags]
 
 - Preview adding a prefix: `renamer insert ^ "[2025] " --dry-run`
 - Append before extension: `renamer insert $ _ARCHIVE --yes --path ./docs`
+- Insert before the final character: `renamer insert 1$ _TAIL --path ./images --dry-run`
 - Insert after third character in stem: `renamer insert 3 _tag --path ./images --dry-run`
 - Combine with extension filter: `renamer insert ^ "v1_" --extensions .txt|.md`
 
diff --git a/internal/insert/positions.go b/internal/insert/positions.go
index be8569d..82579ac 100644
--- a/internal/insert/positions.go
+++ b/internal/insert/positions.go
@@ -3,6 +3,7 @@ package insert
 import (
 	"errors"
 	"fmt"
+	"strings"
 	"unicode/utf8"
 )
 
@@ -11,8 +12,12 @@ type Position struct {
 	Index int // zero-based index where insertion should occur
 }
 
-// ResolvePosition interprets a position token (`^`, `$`, positive, negative) against the stem length.
+// ResolvePosition interprets a position token (`^`, `$`, forward indexes, suffix offsets like `N$`, or legacy negative values) against the stem length.
 func ResolvePosition(token string, stemLength int) (Position, error) {
+	if token == "" {
+		return Position{}, errors.New("position token cannot be empty")
+	}
+
 	switch token {
 	case "^":
 		return Position{Index: 0}, nil
@@ -20,8 +25,40 @@ func ResolvePosition(token string, stemLength int) (Position, error) {
 		return Position{Index: stemLength}, nil
 	}
 
-	if token == "" {
-		return Position{}, errors.New("position token cannot be empty")
+	if strings.HasPrefix(token, "^") {
+		trimmed := token[1:]
+		if trimmed == "" {
+			return Position{Index: 0}, nil
+		}
+		value, err := parseInt(trimmed)
+		if err != nil {
+			return Position{}, fmt.Errorf("invalid position token %q: %w", token, err)
+		}
+		if value < 0 {
+			return Position{}, fmt.Errorf("invalid position token %q: cannot be negative", token)
+		}
+		if value > stemLength {
+			return Position{}, fmt.Errorf("position %d out of range for %d-character stem", value, stemLength)
+		}
+		return Position{Index: value}, nil
+	}
+
+	if strings.HasSuffix(token, "$") {
+		trimmed := token[:len(token)-1]
+		if trimmed == "" {
+			return Position{Index: stemLength}, nil
+		}
+		value, err := parseInt(trimmed)
+		if err != nil {
+			return Position{}, fmt.Errorf("invalid position token %q: %w", token, err)
+		}
+		if value < 0 {
+			return Position{}, fmt.Errorf("invalid position token %q: cannot be negative", token)
+		}
+		if value > stemLength {
+			return Position{}, fmt.Errorf("position %d out of range for %d-character stem", value, stemLength)
+		}
+		return Position{Index: stemLength - value}, nil
 	}
 
 	// Try parsing as integer (positive or negative).
diff --git a/specs/005-add-insert-command/quickstart.md b/specs/005-add-insert-command/quickstart.md
index 5a95736..b8983bd 100644
--- a/specs/005-add-insert-command/quickstart.md
+++ b/specs/005-add-insert-command/quickstart.md
@@ -9,9 +9,9 @@
 
 2. **Insert text near the end while preserving extensions.**
    ```bash
-   renamer insert -1 "_FINAL" --path ./reports --dry-run
+   renamer insert 1$ "_FINAL" --path ./reports --dry-run
    ```
-   - `-1` places the string before the last character of the stem.
+   - `1$` places the string before the last character of the stem.
    - Combine with `--extensions` to limit to specific file types.
 
 3. **Commit changes once preview looks correct.**
diff --git a/specs/005-add-insert-command/spec.md b/specs/005-add-insert-command/spec.md
index ca63c39..a8fad43 100644
--- a/specs/005-add-insert-command/spec.md
+++ b/specs/005-add-insert-command/spec.md
@@ -3,7 +3,7 @@
 **Feature Branch**: `005-add-insert-command`  
 **Created**: 2025-10-30  
 **Status**: Draft  
-**Input**: User description: "实现插入（Insert）字符，支持在文件名指定位置插入指定字符串数据，示例 renamer insert <position> <string>, position:可以包含 ^：开头、$：结尾、 正数：字符位置、负数：倒数字符位置。！！重要：需要考虑中文字符"
+**Input**: User description: "实现插入（Insert）字符，支持在文件名指定位置插入指定字符串数据，示例 renamer insert <position> <string>, position:可以包含 ^：开头、$：结尾、 正数：字符位置、使用 N$ 表示倒数第 N 个字符。！！重要：需要考虑中文字符"
 
 ## User Scenarios & Testing *(mandatory)*
 
@@ -18,7 +18,7 @@ As a power user organizing media files, I want to insert a label into filenames
 **Acceptance Scenarios**:
 
 1. **Given** files named `项目A报告.docx` and `项目B报告.docx`, **When** the user runs `renamer insert ^ 2025- --dry-run`, **Then** the preview lists `2025-项目A报告.docx` and `2025-项目B报告.docx`.
-2. **Given** files named `holiday.jpg` and `trip.jpg`, **When** the user runs `renamer insert -1 X --yes`, **Then** the apply step inserts `X` before the last character of each base name while preserving extensions.
+2. **Given** files named `holiday.jpg` and `trip.jpg`, **When** the user runs `renamer insert 1$ X --yes`, **Then** the apply step inserts `X` before the last character of each base name while preserving extensions.
 
 ---
 
@@ -65,13 +65,13 @@ As a user preparing filenames with multilingual characters, I want validation an
 
 ### Functional Requirements
 
-- **FR-001**: CLI MUST provide a dedicated `insert` subcommand accepting a positional argument (`^`, `$`, positive integer, or negative integer) and the string to insert.
+- **FR-001**: CLI MUST provide a dedicated `insert` subcommand accepting a positional argument (`^`, `$`, forward indexes like `3`/`^3`, or backward indexes like `1$`) and the string to insert.
 - **FR-002**: Insert positions MUST be interpreted using Unicode code points on the filename stem (excluding extension) so multi-byte characters count as a single position.
 - **FR-003**: The command MUST support scope flags (`--path`, `--recursive`, `--include-dirs`, `--hidden`, `--extensions`, `--dry-run`, `--yes`) consistent with existing commands.
 - **FR-004**: Preview MUST display original and proposed names, highlighting inserted segments, and block apply when conflicts or invalid positions are detected.
 - **FR-005**: Apply MUST update filesystem entries atomically per batch, record operations in the `.renamer` ledger with inserted string, position rule, affected files, and timestamps, and support undo.
 - **FR-006**: Validation MUST reject positions outside the allowable range, empty insertion strings (unless explicitly allowed), and inputs containing path separators or control characters.
-- **FR-007**: Help output MUST describe position semantics (`^`, `$`, positive, negative), Unicode handling, and examples for both files and directories.
+- **FR-007**: Help output MUST describe position semantics (`^`, `$`, forward indexes, backward suffix tokens such as `N$`), Unicode handling, and examples for both files and directories.
 - **FR-008**: Automation runs with `--yes` MUST emit deterministic exit codes (`0` success, non-zero on validation/conflicts) and human-readable messages that can be parsed for errors.
 
 ### Key Entities
diff --git a/tests/contract/insert_command_test.go b/tests/contract/insert_command_test.go
index b4a9719..73b5f03 100644
--- a/tests/contract/insert_command_test.go
+++ b/tests/contract/insert_command_test.go
@@ -71,6 +71,62 @@ func TestInsertPreviewAndApply(t *testing.T) {
 	}
 }
 
+func TestInsertTailOffsetToken(t *testing.T) {
+	t.Parallel()
+
+	tmp := t.TempDir()
+	writeInsertFile(t, filepath.Join(tmp, "code.txt"))
+
+	scope := &listing.ListingRequest{
+		WorkingDir:         tmp,
+		IncludeDirectories: false,
+		Recursive:          false,
+		IncludeHidden:      false,
+		Extensions:         nil,
+		Format:             listing.FormatTable,
+	}
+	if err := scope.Validate(); err != nil {
+		t.Fatalf("validate scope: %v", err)
+	}
+
+	req := insert.NewRequest(scope)
+	req.SetExecutionMode(true, false)
+	req.SetPositionAndText("1$", "_TAIL")
+
+	summary, planned, err := insert.Preview(context.Background(), req, nil)
+	if err != nil {
+		t.Fatalf("preview error: %v", err)
+	}
+	if summary.TotalCandidates != 1 {
+		t.Fatalf("expected 1 candidate, got %d", summary.TotalCandidates)
+	}
+	if summary.TotalChanged != 1 {
+		t.Fatalf("expected 1 change, got %d", summary.TotalChanged)
+	}
+	if len(planned) != 1 {
+		t.Fatalf("expected 1 planned operation, got %d", len(planned))
+	}
+	expected := filepath.ToSlash("cod_TAILe.txt")
+	if planned[0].ProposedRelative != expected {
+		t.Fatalf("expected proposed path %s, got %s", expected, planned[0].ProposedRelative)
+	}
+
+	req.SetExecutionMode(false, true)
+	entry, err := insert.Apply(context.Background(), req, planned, summary)
+	if err != nil {
+		t.Fatalf("apply error: %v", err)
+	}
+	if len(entry.Operations) != 1 {
+		t.Fatalf("expected 1 ledger entry, got %d", len(entry.Operations))
+	}
+	if _, err := os.Stat(filepath.Join(tmp, "cod_TAILe.txt")); err != nil {
+		t.Fatalf("expected renamed file cod_TAILe.txt: %v", err)
+	}
+	if _, err := os.Stat(filepath.Join(tmp, "code.txt")); !errors.Is(err, os.ErrNotExist) {
+		t.Fatalf("expected original file to be renamed, err=%v", err)
+	}
+}
+
 func writeInsertFile(t *testing.T, path string) {
 	t.Helper()
 	if err := os.MkdirAll(filepath.Dir(path), 0o755); err != nil {
diff --git a/tests/contract/insert_ledger_test.go b/tests/contract/insert_ledger_test.go
index 93fa0c2..f7002a6 100644
--- a/tests/contract/insert_ledger_test.go
+++ b/tests/contract/insert_ledger_test.go
@@ -95,6 +95,52 @@ func TestInsertZeroMatchExitsSuccessfully(t *testing.T) {
 	}
 }
 
+func TestInsertLedgerCapturesTailOffsetToken(t *testing.T) {
+	t.Parallel()
+
+	tmp := t.TempDir()
+	writeInsertLedgerFile(t, filepath.Join(tmp, "ab.txt"))
+
+	scope := &listing.ListingRequest{
+		WorkingDir:         tmp,
+		IncludeDirectories: false,
+		Recursive:          false,
+		IncludeHidden:      false,
+		Format:             listing.FormatTable,
+	}
+	if err := scope.Validate(); err != nil {
+		t.Fatalf("validate scope: %v", err)
+	}
+
+	req := insert.NewRequest(scope)
+	req.SetExecutionMode(false, true)
+	req.SetPositionAndText("1$", "_SUFFIX")
+
+	summary, planned, err := insert.Preview(context.Background(), req, nil)
+	if err != nil {
+		t.Fatalf("preview error: %v", err)
+	}
+	if len(planned) != 1 {
+		t.Fatalf("expected 1 planned operation, got %d", len(planned))
+	}
+
+	entry, err := insert.Apply(context.Background(), req, planned, summary)
+	if err != nil {
+		t.Fatalf("apply error: %v", err)
+	}
+
+	if entry.Metadata["positionToken"] != "1$" {
+		t.Fatalf("expected position token metadata 1$, got %v", entry.Metadata["positionToken"])
+	}
+	if entry.Metadata["insertText"] != "_SUFFIX" {
+		t.Fatalf("expected insertText metadata _SUFFIX, got %v", entry.Metadata["insertText"])
+	}
+
+	if _, err := os.Stat(filepath.Join(tmp, "a_SUFFIXb.txt")); err != nil {
+		t.Fatalf("expected renamed file a_SUFFIXb.txt: %v", err)
+	}
+}
+
 func writeInsertLedgerFile(t *testing.T, path string) {
 	t.Helper()
 	if err := os.MkdirAll(filepath.Dir(path), 0o755); err != nil {
diff --git a/tests/integration/insert_flow_test.go b/tests/integration/insert_flow_test.go
index 79cb5a1..c4c0b7b 100644
--- a/tests/integration/insert_flow_test.go
+++ b/tests/integration/insert_flow_test.go
@@ -48,6 +48,30 @@ func TestInsertCommandFlow(t *testing.T) {
 	}
 }
 
+func TestInsertCommandTailOffsetToken(t *testing.T) {
+	t.Parallel()
+
+	tmp := t.TempDir()
+	createInsertFile(t, filepath.Join(tmp, "demo.txt"))
+
+	var out bytes.Buffer
+	cmd := renamercmd.NewRootCommand()
+	cmd.SetOut(&out)
+	cmd.SetErr(&out)
+	cmd.SetArgs([]string{"insert", "1$", "_TAIL", "--yes", "--path", tmp})
+
+	if err := cmd.Execute(); err != nil {
+		t.Fatalf("insert command failed: %v\noutput: %s", err, out.String())
+	}
+
+	if _, err := os.Stat(filepath.Join(tmp, "dem_TAILo.txt")); err != nil {
+		t.Fatalf("expected dem_TAILo.txt after apply: %v", err)
+	}
+	if _, err := os.Stat(filepath.Join(tmp, "demo.txt")); !os.IsNotExist(err) {
+		t.Fatalf("expected original demo.txt to be renamed, err=%v", err)
+	}
+}
+
 func contains(t *testing.T, haystack string, expected ...string) bool {
 	t.Helper()
 	for _, s := range expected {