diff --git a/land-and-deploy/SKILL.md b/land-and-deploy/SKILL.md
index 74fa527cd..7c781b98e 100644
--- a/land-and-deploy/SKILL.md
+++ b/land-and-deploy/SKILL.md
@@ -1479,13 +1479,25 @@ Record the start timestamp for timing data. Also record which merge path is take
 Try auto-merge first (respects repo merge settings and merge queues):
 
 ```bash
-gh pr merge --auto --delete-branch
+gh pr merge --squash --auto --delete-branch
 ```
 
 If `--auto` succeeds: record `MERGE_PATH=auto`. This means the repo has auto-merge enabled
 and may use merge queues.
 
-If `--auto` is not available (repo doesn't have auto-merge enabled), merge directly:
+`--auto` fails for two unrelated reasons. Both fall through to the direct merge below, so
+the flow is unaffected — but do not report the second one as "auto-merge is disabled":
+
+1. **Auto-merge is disabled for the repo** — `Auto-merge is not allowed for this repository`.
+2. **The PR is not waiting on anything.** `--auto` only *queues* a merge behind pending
+   required checks. When every required check has already settled — or the repo declares
+   no required status checks at all — GitHub treats the PR as immediately mergeable and
+   rejects the mutation:
+   `Pull request is in clean status` (everything green) or
+   `Pull request is in unstable status` (something red, but nothing required).
+   A repo with zero required status checks therefore takes the direct path 100% of the
+   time no matter how auto-merge is configured, and so does any repo whose CI finishes
+   before this step runs.
 
 ```bash
 gh pr merge --squash --delete-branch
diff --git a/land-and-deploy/SKILL.md.tmpl b/land-and-deploy/SKILL.md.tmpl
index 98976ad02..78c3cffc2 100644
--- a/land-and-deploy/SKILL.md.tmpl
+++ b/land-and-deploy/SKILL.md.tmpl
@@ -598,13 +598,25 @@ Record the start timestamp for timing data. Also record which merge path is take
 Try auto-merge first (respects repo merge settings and merge queues):
 
 ```bash
-gh pr merge --auto --delete-branch
+gh pr merge --squash --auto --delete-branch
 ```
 
 If `--auto` succeeds: record `MERGE_PATH=auto`. This means the repo has auto-merge enabled
 and may use merge queues.
 
-If `--auto` is not available (repo doesn't have auto-merge enabled), merge directly:
+`--auto` fails for two unrelated reasons. Both fall through to the direct merge below, so
+the flow is unaffected — but do not report the second one as "auto-merge is disabled":
+
+1. **Auto-merge is disabled for the repo** — `Auto-merge is not allowed for this repository`.
+2. **The PR is not waiting on anything.** `--auto` only *queues* a merge behind pending
+   required checks. When every required check has already settled — or the repo declares
+   no required status checks at all — GitHub treats the PR as immediately mergeable and
+   rejects the mutation:
+   `Pull request is in clean status` (everything green) or
+   `Pull request is in unstable status` (something red, but nothing required).
+   A repo with zero required status checks therefore takes the direct path 100% of the
+   time no matter how auto-merge is configured, and so does any repo whose CI finishes
+   before this step runs.
 
 ```bash
 gh pr merge --squash --delete-branch
diff --git a/scripts/gen-skill-docs.ts b/scripts/gen-skill-docs.ts
index 6d70206cd..a19833b44 100644
--- a/scripts/gen-skill-docs.ts
+++ b/scripts/gen-skill-docs.ts
@@ -806,7 +806,12 @@ function processExternalHost(
 }
 
 function processTemplate(tmplPath: string, host: Host = 'claude'): { outputPath: string; content: string; symlinkLoop?: boolean; catalogParts?: CatalogParts | null } {
-  const tmplContent = fs.readFileSync(tmplPath, 'utf-8');
+  // Normalize to LF at the entry point. Templates may have CRLF on disk when
+  // checked out on Windows with core.autocrlf=true. Downstream regexes
+  // (processVoiceTriggers, transformFrontmatter) hardcode \n, so without
+  // normalization they silently no-op on CRLF — producing different output
+  // than CI (Linux, LF) and breaking the Skill Docs Freshness check.
+  const tmplContent = fs.readFileSync(tmplPath, 'utf-8').replace(/\r\n/g, '\n');
   const relTmplPath = path.relative(ROOT, tmplPath);
   let outputPath = tmplPath.replace(/\.tmpl$/, '');