diff --git a/src/prompts/maestro-system-prompt.md b/src/prompts/maestro-system-prompt.md
index 63691259..63327980 100644
--- a/src/prompts/maestro-system-prompt.md
+++ b/src/prompts/maestro-system-prompt.md
@@ -21,7 +21,7 @@ Maestro is an Electron desktop application for managing multiple AI coding assis
 
 ## Auto-run Documents
 
-When a user wants an auto-run document, create a detailed multi-document, multi-point Markdown implementation plan in the `{{AUTORUN_FOLDER}}` folder. Use the format `$PREFIX-X.md`, where `X` is the phase number and `$PREFIX` is the effort name. Break phases by relevant context; do not mix unrelated task results in the same document. If working within a file, group and fix all type issues in that file together. If working with an MCP, keep all related tasks in the same document. Each task must be written as `- [ ] ...` so auto-run can execute and check them off with comments on completion. This is token-heavy, so be deliberate about document count and task granularity.
+When a user wants an auto-run document, create a detailed multi-document, multi-point Markdown implementation plan in the `{{AUTORUN_FOLDER}}` folder. Use the format `$PREFIX-XX.md`, where `XX` is the two-digit phase number (01, 02, etc.) and `$PREFIX` is the effort name. Always zero-pad phase numbers to ensure correct lexicographic sorting. Break phases by relevant context; do not mix unrelated task results in the same document. If working within a file, group and fix all type issues in that file together. If working with an MCP, keep all related tasks in the same document. Each task must be written as `- [ ] ...` so auto-run can execute and check them off with comments on completion. This is token-heavy, so be deliberate about document count and task granularity.
 
 **Note:** The Auto Run folder may be located outside your working directory (e.g., in a parent repository when you are in a worktree). This is intentional - always use the exact path specified above for Auto Run documents.
 
diff --git a/src/prompts/wizard-inline-new.md b/src/prompts/wizard-inline-new.md
index 418857ed..0ebdc724 100644
--- a/src/prompts/wizard-inline-new.md
+++ b/src/prompts/wizard-inline-new.md
@@ -25,7 +25,7 @@ This restriction ensures the wizard can safely run in parallel with other AI ope
 
 ## Auto-run Documents
 
-When creating Playbooks, generate detailed multi-document Markdown implementation plans in the `{{AUTORUN_FOLDER}}` folder. Use the format `$PREFIX-X.md`, where `X` is the phase number and `$PREFIX` is the effort name. Break phases by relevant context; do not mix unrelated task results in the same document. Each task must be written as `- [ ] ...` so auto-run can execute and check them off with comments on completion.
+When creating Playbooks, generate detailed multi-document Markdown implementation plans in the `{{AUTORUN_FOLDER}}` folder. Use the format `$PREFIX-XX.md`, where `XX` is the two-digit phase number (01, 02, etc.) and `$PREFIX` is the effort name. Always zero-pad phase numbers to ensure correct lexicographic sorting. Break phases by relevant context; do not mix unrelated task results in the same document. Each task must be written as `- [ ] ...` so auto-run can execute and check them off with comments on completion.
 
 ## Your Goal