diff --git a/cmd/root.go b/cmd/root.go
index a837216..50f06c3 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -65,6 +65,7 @@ func init() {
 	rootCmd.AddCommand(scaffoldCmd)
 	rootCmd.AddCommand(queryCmd)
 	rootCmd.AddCommand(analyzeCmd)
+	rootCmd.AddCommand(workonCmd)
 
 	// Add model flag to all commands
 	rootCmd.PersistentFlags().StringP("model", "m", "", "Grok model to use (overrides config)")
diff --git a/cmd/workon.go b/cmd/workon.go
new file mode 100644
index 0000000..ed230f4
--- /dev/null
+++ b/cmd/workon.go
@@ -0,0 +1,60 @@
+package cmd
+
+import (
+	"fmt"
+	"strings"
+
+	"github.com/fatih/color"
+	"github.com/spf13/cobra"
+
+	"gmgauthier.com/grokkit/internal/logger"
+	"gmgauthier.com/grokkit/internal/workon"
+)
+
+var workonCmd = &cobra.Command{
+	Use:   "workon <todo_item_title>",
+	Short: "Start or complete work on a todo item or fix",
+	Long: `workon automates starting or completing a todo/fix:
+- Moves queued todo to doing/ or creates new fix .md
+- Creates matching git branch
+- Generates + appends "Work Plan" via Grok
+- Commits to the branch
+- Optional: cnadd log + open in configured IDE
+
+Purely transactional. See todo/doing/workon.md for full spec.`,
+	Args: cobra.ExactArgs(1),
+	RunE: func(cmd *cobra.Command, args []string) error {
+		title := strings.ReplaceAll(args[0], " ", "-")
+		customMsg, _ := cmd.Flags().GetString("message")
+		isFix, _ := cmd.Flags().GetBool("fix")
+		isComplete, _ := cmd.Flags().GetBool("complete")
+
+		if isComplete && customMsg != "" {
+			return fmt.Errorf("-c cannot be combined with -m")
+		}
+
+		logger.Info("workon starting", "title", title, "fix", isFix, "complete", isComplete)
+
+		if err := workon.Run(title, customMsg, isFix, isComplete); err != nil {
+			color.Red("workon failed: %v", err)
+			return err
+		}
+
+		mode := "todo"
+		if isFix {
+			mode = "fix"
+		}
+		action := "started"
+		if isComplete {
+			action = "completed"
+		}
+		color.Green("workon %s: %s (%s)", action, title, mode)
+		return nil
+	},
+}
+
+func init() {
+	workonCmd.Flags().StringP("message", "M", "", "Custom commit message (default: \"Start working on <todo_item_title>\")")
+	workonCmd.Flags().BoolP("fix", "f", false, "Treat as fix instead of todo (create new .md in doing/)")
+	workonCmd.Flags().BoolP("complete", "c", false, "Complete the item (move to completed/; exclusive)")
+}
diff --git a/config.toml.example b/config.toml.example
index 1929a0c..71c0087 100644
--- a/config.toml.example
+++ b/config.toml.example
@@ -23,6 +23,8 @@ fast = "grok-4-1-fast-non-reasoning"
   history.model = "grok-4"
   prdescribe.model = "grok-4"
   review.model = "grok-4"
+  workon.model = "grok-4-1-fast-non-reasoning"  # Fast model for work plan generation
+  workon.ide = ""                                # IDE command to open repo (e.g. "code", "goland")
 
 # Chat history settings
 [chat]
diff --git a/config/config.go b/config/config.go
index 36816a9..68df4b0 100644
--- a/config/config.go
+++ b/config/config.go
@@ -38,6 +38,8 @@ func Load() {
 	viper.SetDefault("commands.review.model", "grok-4")
 	viper.SetDefault("commands.docs.model", "grok-4")
 	viper.SetDefault("commands.query.model", "grok-4-1-fast-non-reasoning")
+	viper.SetDefault("commands.workon.model", "grok-4-1-fast-non-reasoning")
+	viper.SetDefault("commands.workon.ide", "")
 
 	// Config file is optional, so we ignore read errors
 	_ = viper.ReadInConfig()
@@ -72,6 +74,11 @@ func GetTimeout() int {
 	return timeout
 }
 
+// GetIDECommand returns the configured IDE command for workon, or empty string if unset.
+func GetIDECommand() string {
+	return viper.GetString("commands.workon.ide")
+}
+
 // GetLogLevel returns the log level from the configuration
 func GetLogLevel() string {
 	return viper.GetString("log_level")
diff --git a/internal/todo/todo.go b/internal/todo/todo.go
new file mode 100644
index 0000000..417a0e8
--- /dev/null
+++ b/internal/todo/todo.go
@@ -0,0 +1,28 @@
+package todo
+
+import (
+	"os"
+	"path/filepath"
+)
+
+const todoRoot = "todo"
+
+// Bootstrap creates the todo folder structure + basic index if missing.
+func Bootstrap() error {
+	dirs := []string{
+		filepath.Join(todoRoot, "queued"),
+		filepath.Join(todoRoot, "doing"),
+		filepath.Join(todoRoot, "completed"),
+	}
+	for _, d := range dirs {
+		if err := os.MkdirAll(d, 0755); err != nil {
+			return err
+		}
+	}
+	// Basic index README stub
+	index := filepath.Join(todoRoot, "README.md")
+	if _, err := os.Stat(index); os.IsNotExist(err) {
+		return os.WriteFile(index, []byte("# Todo Index\n\n## Queued\n## Doing\n## Completed\n"), 0644)
+	}
+	return nil
+}
diff --git a/internal/workon/workon.go b/internal/workon/workon.go
new file mode 100644
index 0000000..2d23362
--- /dev/null
+++ b/internal/workon/workon.go
@@ -0,0 +1,222 @@
+package workon
+
+import (
+	"fmt"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"strings"
+
+	"gmgauthier.com/grokkit/config"
+	"gmgauthier.com/grokkit/internal/grok"
+	"gmgauthier.com/grokkit/internal/logger"
+	"gmgauthier.com/grokkit/internal/todo"
+)
+
+// Run executes the full transactional workon flow per todo/doing/workon.md spec.
+func Run(title, customMsg string, isFix, isComplete bool) error {
+	if title == "" {
+		return fmt.Errorf("todo_item_title is required")
+	}
+
+	logger.Info("workon starting", "title", title, "fix", isFix, "complete", isComplete)
+
+	// 1. Bootstrap todo structure if missing
+	if err := todo.Bootstrap(); err != nil {
+		return fmt.Errorf("todo bootstrap failed: %w", err)
+	}
+
+	if isComplete {
+		return completeItem(title, isFix)
+	}
+
+	// 2. Handle todo or fix mode
+	branchPrefix := "feature/"
+	if isFix {
+		branchPrefix = "fix/"
+	}
+	branchName := branchPrefix + title
+	mdPath := filepath.Join("todo", "doing", title+".md")
+
+	if isFix {
+		if err := createFixFile(mdPath, title); err != nil {
+			return fmt.Errorf("create fix file failed: %w", err)
+		}
+	} else {
+		if err := moveQueuedToDoing(title); err != nil {
+			return fmt.Errorf("move to doing failed: %w", err)
+		}
+	}
+
+	// 3. Create git branch (safe)
+	if err := createGitBranch(branchName); err != nil {
+		return fmt.Errorf("failed to create branch %s: %w", branchName, err)
+	}
+
+	// 4. Generate + append Work Plan via Grok
+	if err := appendWorkPlan(mdPath, title); err != nil {
+		return fmt.Errorf("failed to generate/append Work Plan: %w", err)
+	}
+
+	// 5. Commit
+	commitMsg := customMsg
+	if commitMsg == "" {
+		commitMsg = fmt.Sprintf("Start working on %s", title)
+	}
+	if err := commitChanges(commitMsg); err != nil {
+		return fmt.Errorf("commit failed: %w", err)
+	}
+
+	// 6. Optional post-steps (graceful)
+	runCnaddIfAvailable(title)
+	openIDEIfConfigured()
+
+	logger.Info("workon transaction complete", "branch", branchName, "mode", map[bool]string{true: "fix", false: "todo"}[isFix])
+	return nil
+}
+
+func moveQueuedToDoing(title string) error {
+	src := filepath.Join("todo", "queued", title+".md")
+	dst := filepath.Join("todo", "doing", title+".md")
+	if err := os.Rename(src, dst); err != nil {
+		return fmt.Errorf("move %s -> doing failed: %w", title, err)
+	}
+	return nil
+}
+
+func createFixFile(path, title string) error {
+	content := fmt.Sprintf("# %s\n\n## Work Plan\n\n", title)
+	return os.WriteFile(path, []byte(content), 0644)
+}
+
+func createGitBranch(name string) error {
+	// Safe: if branch already exists, just checkout it; else create new
+	if err := exec.Command("git", "checkout", name).Run(); err == nil {
+		return nil
+	}
+	return exec.Command("git", "checkout", "-b", name).Run()
+}
+
+func appendWorkPlan(path, title string) error {
+	content := readFileContent(path)
+
+	prompt := fmt.Sprintf(`You are helping implement a todo item titled "%s".
+
+Here is the current markdown content of the todo/fix file:
+
+%s
+
+Generate a concise, actionable **Work Plan** section.
+Use numbered steps. Be specific to this item. Include testing and commit notes where relevant.
+Output ONLY the markdown starting with "## Work Plan" — no extra text, no introduction.`, title, content)
+
+	// Real Grok call using the project's standard client (StreamSilent for clean output)
+	client := grok.NewClient()
+	model := config.GetModel("workon", "")
+	plan := client.StreamSilent([]map[string]string{
+		{"role": "system", "content": "You are a precise software engineering assistant."},
+		{"role": "user", "content": prompt},
+	}, model) // or pull model from config/env if available
+
+	// Append the plan
+	f, err := os.OpenFile(path, os.O_APPEND|os.O_WRONLY, 0644)
+	if err != nil {
+		return err
+	}
+	defer func() {
+		if cerr := f.Close(); cerr != nil {
+			logger.Error("failed to close todo file", "err", cerr)
+		}
+	}()
+	_, err = f.WriteString(plan)
+	return err
+}
+
+func readFileContent(path string) string {
+	b, _ := os.ReadFile(path)
+	return string(b)
+}
+
+func commitChanges(msg string) error {
+	if err := exec.Command("git", "add", "todo/").Run(); err != nil {
+		return err
+	}
+	return exec.Command("git", "commit", "-m", msg).Run()
+}
+
+func completeItem(title string, isFix bool) error {
+	src := filepath.Join("todo", "doing", title+".md")
+	dst := filepath.Join("todo", "completed", title+".md")
+	if err := os.Rename(src, dst); err != nil {
+		return fmt.Errorf("move to completed failed: %w", err)
+	}
+
+	if !isFix {
+		if err := updateReadmeIndex(title); err != nil {
+			logger.Error("failed to update README index", "err", err)
+		}
+	}
+
+	commitMsg := fmt.Sprintf("Complete work on %s", title)
+	if err := commitChanges(commitMsg); err != nil {
+		return fmt.Errorf("complete commit failed: %w", err)
+	}
+	return nil
+}
+
+func updateReadmeIndex(title string) error {
+	readmePath := filepath.Join("todo", "README.md")
+	data, err := os.ReadFile(readmePath)
+	if err != nil {
+		return fmt.Errorf("read README: %w", err)
+	}
+
+	lines := strings.Split(string(data), "\n")
+	var result []string
+	completedIdx := -1
+
+	for i, line := range lines {
+		// Skip the line referencing this title in the Queued section
+		if strings.Contains(line, title+".md") && strings.Contains(line, "queued/") {
+			continue
+		}
+		// Track the last line in the Completed section
+		if strings.HasPrefix(line, "## Completed") {
+			completedIdx = i
+		}
+		result = append(result, line)
+	}
+
+	// Find insertion point: after last non-empty line following ## Completed
+	if completedIdx >= 0 {
+		insertIdx := completedIdx + 1
+		for insertIdx < len(result) && (strings.HasPrefix(result[insertIdx], "*") || strings.TrimSpace(result[insertIdx]) == "") {
+			if strings.HasPrefix(result[insertIdx], "*") {
+				insertIdx++
+			} else {
+				break
+			}
+		}
+		entry := fmt.Sprintf("* [%s](./completed/%s.md) : %s *(done)*", title, title, title)
+		result = append(result[:insertIdx], append([]string{entry}, result[insertIdx:]...)...)
+	}
+
+	return os.WriteFile(readmePath, []byte(strings.Join(result, "\n")), 0644)
+}
+
+func runCnaddIfAvailable(title string) {
+	if _, err := exec.LookPath("cnadd"); err == nil {
+		_ = exec.Command("cnadd", "log", fmt.Sprintf("started work on %s", title)).Run()
+	}
+}
+
+func openIDEIfConfigured() {
+	ideCmd := config.GetIDECommand()
+	if ideCmd == "" {
+		logger.Debug("IDE open skipped (no IDE configured)")
+		return
+	}
+	if err := exec.Command(ideCmd, ".").Start(); err != nil {
+		logger.Error("failed to open IDE", "cmd", ideCmd, "err", err)
+	}
+}
diff --git a/todo/README.md b/todo/README.md
index 2495af8..7ecb6a5 100644
--- a/todo/README.md
+++ b/todo/README.md
@@ -4,7 +4,7 @@ This document provides a table of contents for all tasks and features currently
 
 ## Queued
 
-* [1] [workon](./queued/workon.md): Grokkit workon for bootstrapping a new feature
+* [1] [workon](doing/workon.md): Grokkit workon for bootstrapping a new feature
 * [2] [cnotes.md](./queued/cnotes.md) : grokkit cnotes integration
 * [3] [make.md](./queued/make.md) : grokkit make integration
 * [4] [rg.md](./queued/rg.md) : grokkit ripgrep (rg) integration
diff --git a/todo/queued/workon.md b/todo/doing/workon.md
similarity index 100%
rename from todo/queued/workon.md
rename to todo/doing/workon.md