diff --git a/scripts/resolvers/preamble.ts b/scripts/resolvers/preamble.ts
index dd490202..533864fc 100644
--- a/scripts/resolvers/preamble.ts
+++ b/scripts/resolvers/preamble.ts
@@ -37,6 +37,9 @@ import { generateWritingStyleMigration } from './preamble/generate-writing-style
 // Host-specific instructions
 import { generateBrainHealthInstruction } from './preamble/generate-brain-health-instruction';
 
+// GBrain cross-machine sync (runs at skill start; end-side handled in completion-status)
+import { generateBrainSyncBlock } from './preamble/generate-brain-sync-block';
+
 // Behavioral / voice
 import { generateVoiceDirective } from './preamble/generate-voice-directive';
 
@@ -84,6 +87,7 @@ export function generatePreamble(ctx: TemplateContext): string {
     generateVendoringDeprecation(ctx),
     generateSpawnedSessionCheck(),
     generateBrainHealthInstruction(ctx),
+    generateBrainSyncBlock(ctx),
     generateModelOverlay(ctx),
     generateVoiceDirective(tier),
     ...(tier >= 2 ? [
diff --git a/scripts/resolvers/preamble/generate-brain-sync-block.ts b/scripts/resolvers/preamble/generate-brain-sync-block.ts
new file mode 100644
index 00000000..6a378e58
--- /dev/null
+++ b/scripts/resolvers/preamble/generate-brain-sync-block.ts
@@ -0,0 +1,124 @@
+/**
+ * gbrain-sync preamble block.
+ *
+ * Emits bash that runs at every skill invocation:
+ *   1. If ~/.gstack-brain-remote.txt exists AND ~/.gstack/.git is missing,
+ *      surface a restore-available hint (does NOT auto-run restore).
+ *   2. If sync is on, run `gstack-brain-sync --once` (drain + push).
+ *   3. On first skill of the day (24h cache via .brain-last-pull):
+ *      `git fetch` + ff-only merge (JSONL merge driver handles conflicts).
+ *   4. Emit a `BRAIN_SYNC:` status line so every skill surfaces health.
+ *
+ * Also emits prose instructions for the host LLM to fire a one-time privacy
+ * stop-gate via AskUserQuestion when gbrain_sync_mode is unset and gbrain
+ * is available on the host.
+ *
+ * Block emitted across all tiers. Internal bash short-circuits when feature
+ * is disabled; cost is <5ms.
+ *
+ * Skill-end sync is handled by the completion-status generator via a call
+ * to `gstack-brain-sync --discover-new` + `--once`.
+ */
+import type { TemplateContext } from '../types';
+
+export function generateBrainSyncBlock(ctx: TemplateContext): string {
+  const isBrainHost = ctx.host === 'gbrain' || ctx.host === 'hermes';
+  return `## GBrain Sync (skill start)
+
+\`\`\`bash
+# gbrain-sync: drain pending writes, pull once per day. Silent no-op when
+# the feature isn't initialized or gbrain_sync_mode is "off". See
+# docs/gbrain-sync.md.
+
+_GSTACK_HOME="\${GSTACK_HOME:-$HOME/.gstack}"
+_BRAIN_REMOTE_FILE="$HOME/.gstack-brain-remote.txt"
+_BRAIN_SYNC_BIN="${ctx.paths.binDir}/gstack-brain-sync"
+_BRAIN_CONFIG_BIN="${ctx.paths.binDir}/gstack-config"
+
+_BRAIN_SYNC_MODE=$("$_BRAIN_CONFIG_BIN" get gbrain_sync_mode 2>/dev/null || echo off)
+
+# New-machine hint: URL file present, local .git missing, sync not yet enabled.
+if [ -f "$_BRAIN_REMOTE_FILE" ] && [ ! -d "$_GSTACK_HOME/.git" ] && [ "$_BRAIN_SYNC_MODE" = "off" ]; then
+  _BRAIN_NEW_URL=$(head -1 "$_BRAIN_REMOTE_FILE" 2>/dev/null | tr -d '[:space:]')
+  if [ -n "$_BRAIN_NEW_URL" ]; then
+    echo "BRAIN_SYNC: brain repo detected: $_BRAIN_NEW_URL"
+    echo "BRAIN_SYNC: run 'gstack-brain-restore' to pull your cross-machine memory (or 'gstack-config set gbrain_sync_mode off' to dismiss forever)"
+  fi
+fi
+
+# Active-sync path.
+if [ -d "$_GSTACK_HOME/.git" ] && [ "$_BRAIN_SYNC_MODE" != "off" ]; then
+  # Once-per-day pull.
+  _BRAIN_LAST_PULL_FILE="$_GSTACK_HOME/.brain-last-pull"
+  _BRAIN_NOW=$(date +%s)
+  _BRAIN_DO_PULL=1
+  if [ -f "$_BRAIN_LAST_PULL_FILE" ]; then
+    _BRAIN_LAST=$(cat "$_BRAIN_LAST_PULL_FILE" 2>/dev/null || echo 0)
+    _BRAIN_AGE=$(( _BRAIN_NOW - _BRAIN_LAST ))
+    [ "$_BRAIN_AGE" -lt 86400 ] && _BRAIN_DO_PULL=0
+  fi
+  if [ "$_BRAIN_DO_PULL" = "1" ]; then
+    ( cd "$_GSTACK_HOME" && git fetch origin >/dev/null 2>&1 && git merge --ff-only "origin/$(git rev-parse --abbrev-ref HEAD)" >/dev/null 2>&1 ) || true
+    echo "$_BRAIN_NOW" > "$_BRAIN_LAST_PULL_FILE"
+  fi
+  # Drain pending queue, push.
+  "$_BRAIN_SYNC_BIN" --once 2>/dev/null || true
+fi
+
+# Status line — always emitted, easy to grep.
+if [ -d "$_GSTACK_HOME/.git" ] && [ "$_BRAIN_SYNC_MODE" != "off" ]; then
+  _BRAIN_QUEUE_DEPTH=0
+  [ -f "$_GSTACK_HOME/.brain-queue.jsonl" ] && _BRAIN_QUEUE_DEPTH=$(wc -l < "$_GSTACK_HOME/.brain-queue.jsonl" | tr -d ' ')
+  _BRAIN_LAST_PUSH="never"
+  [ -f "$_GSTACK_HOME/.brain-last-push" ] && _BRAIN_LAST_PUSH=$(cat "$_GSTACK_HOME/.brain-last-push" 2>/dev/null || echo never)
+  echo "BRAIN_SYNC: mode=$_BRAIN_SYNC_MODE | last_push=$_BRAIN_LAST_PUSH | queue=$_BRAIN_QUEUE_DEPTH"
+else
+  echo "BRAIN_SYNC: off"
+fi
+\`\`\`
+
+${isBrainHost ? `If the bash output shows \`BRAIN_SYNC: brain repo detected\`, the user copied their remote URL file to this machine but hasn't restored yet. Offer to run \`gstack-brain-restore\` via AskUserQuestion. If the user agrees, run the command; otherwise continue without sync.` : ''}
+
+**Privacy stop-gate (fires ONCE per machine).**
+
+If the bash output shows \`BRAIN_SYNC: off\` AND the config value
+\`gbrain_sync_mode_prompted\` is \`false\` AND gbrain is detected on this host
+(either \`gbrain doctor --fast --json\` succeeds or the \`gbrain\` binary is in PATH),
+fire a one-time privacy gate via AskUserQuestion:
+
+> gstack can publish your session memory (learnings, plans, designs, retros) to a
+> private GitHub repo that GBrain indexes across your machines. Higher tiers
+> include behavioral data (session timelines, developer profile). How much do you
+> want to sync?
+
+Options:
+- A) Everything allowlisted (recommended — maximum cross-machine memory)
+- B) Only artifacts (plans, designs, retros, learnings) — skip timelines and profile
+- C) Decline — keep everything local
+
+After the user answers, run (substituting the chosen value):
+
+\`\`\`bash
+# Chosen mode: full | artifacts-only | off
+"$_BRAIN_CONFIG_BIN" set gbrain_sync_mode <choice>
+"$_BRAIN_CONFIG_BIN" set gbrain_sync_mode_prompted true
+\`\`\`
+
+If A or B was chosen AND \`~/.gstack/.git\` doesn't exist, ask a follow-up:
+"Set up the GBrain sync repo now? (runs \`gstack-brain-init\`)"
+- A) Yes, run it now
+- B) Show me the command, I'll run it myself
+
+Do not block the skill. Emit the question, continue the skill workflow. The
+next skill run picks up wherever this left off.
+
+**At skill END (before the telemetry block),** run these bash commands to
+catch artifact writes (design docs, plans, retros) that skipped the writer
+shims, plus drain any still-pending queue entries:
+
+\`\`\`bash
+"${ctx.paths.binDir}/gstack-brain-sync" --discover-new 2>/dev/null || true
+"${ctx.paths.binDir}/gstack-brain-sync" --once 2>/dev/null || true
+\`\`\`
+`;
+}