diff --git a/RUNEWAGER_FUNCTIONALITY_MAP.md b/RUNEWAGER_FUNCTIONALITY_MAP.md
index 8c06eda..eb48946 100644
--- a/RUNEWAGER_FUNCTIONALITY_MAP.md
+++ b/RUNEWAGER_FUNCTIONALITY_MAP.md
@@ -1,6 +1,6 @@
 # RUNEWAGER_FUNCTIONALITY_MAP.md
 
-_Last audited: 2026-02-26_
+_Last audited: 2026-02-28_
 _Source of truth files: `index.js`, `test/*.test.js`, scripts under `scripts/`, deployment/runtime docs in repo root._
 
 ---
@@ -11,7 +11,7 @@ Runewager is a Telegraf-based Telegram bot that provides:
 - User onboarding (age gate, account/Discord guidance, username linking).
 - Promo flows (DB-backed promo manager + eligibility + claim lifecycle).
 - Giveaway flows (creation, join, eligibility checks, auto finalization, admin controls).
-- Content Drops (scheduled/random posts to configured target chat).
+- Helpful Tooltips (scheduled/random posts to configured target chat; formerly "Content Drops").
 - Admin operations (broadcasts, diagnostics, SSHV console, bug triage, backups).
 - Runtime health and deploy tooling (`/health`, scripts, systemd template).
 
@@ -25,7 +25,7 @@ Navigation is driven by inline menus plus command aliases. Persistent user/admin
 - Per-user mutable state stored in memory and persisted to JSON runtime snapshots.
 
 ### State/storage layers
-- In-memory stores: users, giveaway state, analytics, promo manager store, content drops store, broadcast config, SSHV sessions.
+- In-memory stores: users, giveaway state, analytics, promo manager store, helpful tooltips store (`tipsStore`), broadcast config, SSHV sessions.
 - File persistence under `data/` (runtime snapshots + promo DB + optional backups).
 - Periodic persistence timer + startup restore.
 
@@ -80,10 +80,10 @@ Navigation is driven by inline menus plus command aliases. Persistent user/admin
 - System & Health
 - Tests & Bugs
 - VPS Console (/sshv)
-- Content Drops manager shortcut
+- Helpful Tooltips manager shortcut
 
 ### Admin category menus
-- TestAll engine (`/testall`) runs structured diagnostics across environment, data/stores, callbacks/commands, navigation helpers, giveaway/promo/content-drop, SSHV, and pendingAction timeout/label rules; summary line: `TestAll complete — X passed, Y warnings, Z failures.`
+- TestAll engine (`/testall`) runs structured diagnostics across environment, data/stores, callbacks/commands, navigation helpers, giveaway/promo/helpful-tooltips, SSHV, pendingAction timeout/label rules; summary line: `TestAll complete — X passed, Y warnings, Z failures.`
 - `admin_cat_giveaway`: start/test/status + persistent navigation row (`Admin Dashboard`, `Main Menu`, `Cancel`).
 - `admin_cat_promo`: full promo manager actions + guide + persistent navigation row (`Admin Dashboard`, `Main Menu`, `Cancel`).
 - `admin_cat_system`: health/version/verify/setup/backup/admin mode/testall/sshv + persistent navigation row (`Admin Dashboard`, `Main Menu`, `Cancel`).
@@ -234,7 +234,7 @@ Pending-action timeout handling is enforced in the text input router: each pendi
 ### Verification controls
 - Smoke test enforces `REGISTERED_COMMANDS` parity with command handlers detected from `bot.command(...)` and `registerCommand(...)`, including single/double/backtick literals and simple const-driven names (except `start`, handled by `bot.start`).
 - Callback coverage smoke check ignores catch-all callback fallbacks using robust pattern detection (`/.*/`, `/^.*$/`, `/.+/` with optional flags/whitespace), so button coverage must be satisfied by literal handlers or meaningful regex families.
-- Smoke checks assert presence of critical 2.0 command families (onboarding/promo/giveaway/content-drops/admin tools) and pending-action escape routes (`/cancel`, `/menu`, `/start`, `/help`).
+- Smoke checks assert presence of critical 2.0 command families (onboarding/promo/giveaway/helpful-tooltips/admin tools) and pending-action escape routes (`/cancel`, `/menu`, `/start`, `/help`).
 - Smoke checks verify `.env.example` documents core runtime configuration keys used by production flows (Telegram links, HTTPS cert/key paths, mini-app URLs, Discord links, `BOT_PRIVACY_MODE`).
 
 
@@ -308,24 +308,50 @@ admin_cmd_announce_start or /announce
       -> summary result
 ```
 
-### Content drop target registration
+### Helpful Tooltip target registration
 ```text
-Admin forwards message from channel/group
-   -> autoRegisterForwardedChatIfPresent
-   -> approvedGroupsStore add(chatId)
+Admin taps "Link Channel/Group" in Tooltip Settings OR forwards any group/channel message
+   -> extractForwardedChat -> chatId + title extracted
+   -> await_tip_link_target or autoRegisterForwardedChatIfPresent
+   -> approvedGroupsStore.add(chatId)
    -> tipsStore.targetGroup = chatId
+   -> tipsStore.targetGroupTitle = title
    -> broadcastConfigStore.targetGroup = chatId
+   -> confirmation to admin (title + id)
 ```
 
-### Giveaway start/join
+### Helpful Tooltip inline button syntax
+```text
+Tooltip text:
+   <tooltip text here>
+   [Label - https://url] && [Label2 - https://url2]   ← same row
+   [Label3 - https://url3]                             ← new row
+   [Open Bot]                                          ← standard "Open Bot" button
+
+parseTooltipButtons() strips button lines from text and builds Telegraf inlineKeyboard.
+URL validation + label presence enforced; admin receives error message on malformed syntax.
+```
+
+### Giveaway start/join (v3.0+)
 ```text
 Admin starts wizard (gwiz)
-  -> collect config steps
+  -> giveawayPreflightCheck: validates group linked, warns if missing pin permission
+  -> collect config steps (9-step wizard)
   -> createGiveaway + announceGiveaway
+     -> post announcement to group
+     -> pin announcement (notify admin if permission missing)
+     -> scheduleGiveawayRefresh: timers at 25%, 50%, 75% of duration
+        -> each fires: edit/resend message, re-pin
+     -> scheduleGiveawayReminders: 10m, 5m, 1m, 30s, 10→1 countdown messages
   -> users click gw_join_<id>
      -> evaluateEligibility
      -> join accepted/rejected
   -> timer expires -> finalizeGiveaway
+     -> HTML winners announcement in group (parse_mode: HTML)
+     -> DM each winner with SC amount, boost status, "tip has been sent" notice
+     -> admin DM: full report (TG handle, display name, RW username, prize, boost)
+       + "View Results in Group" deep-link button
+       + Reroll/Mark Paid inline actions
 ```
 
 ## 24. Future Updates Log
diff --git a/add_tooltip.sh b/add_tooltip.sh
new file mode 100755
index 0000000..e1d5066
--- /dev/null
+++ b/add_tooltip.sh
@@ -0,0 +1,63 @@
+#!/usr/bin/env bash
+# add_tooltip.sh — Append a new placeholder tooltip entry to tooltips.json.
+# Called by the bot admin panel "Add Tooltip (Script)" button, or manually.
+#
+# Usage:
+#   ./add_tooltip.sh [--text "Custom tooltip text"]
+#
+# Outputs: new tooltip ID on stdout.
+# On success exits 0; on failure exits non-zero.
+
+set -euo pipefail
+
+SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
+APP_DIR="${RUNEWAGER_DIR:-$SCRIPT_DIR}"
+DATA_DIR="$APP_DIR/data"
+TOOLTIPS_FILE="$DATA_DIR/tooltips.json"
+TMP_FILE="$TOOLTIPS_FILE.tmp.$$"
+
+CUSTOM_TEXT=""
+while [[ $# -gt 0 ]]; do
+  case "$1" in
+    --text) CUSTOM_TEXT="$2"; shift 2 ;;
+    *) shift ;;
+  esac
+done
+
+info()  { echo "[add_tooltip] INFO:  $*"; }
+error() { echo "[add_tooltip] ERROR: $*" >&2; exit 1; }
+
+mkdir -p "$DATA_DIR" || error "Cannot create data dir"
+
+# Ensure tooltips.json exists
+if [[ ! -f "$TOOLTIPS_FILE" ]]; then
+  info "tooltips.json not found — initialising empty list"
+  echo '[]' > "$TOOLTIPS_FILE"
+fi
+
+# Validate existing file
+node -e "JSON.parse(require('fs').readFileSync('$TOOLTIPS_FILE','utf8'))" 2>/dev/null \
+  || error "Existing $TOOLTIPS_FILE is not valid JSON"
+
+TOOLTIP_TEXT="${CUSTOM_TEXT:-New tooltip — edit in admin panel via /tips.}"
+
+# Append new entry and get new ID using Node.js
+NEW_ID=$(node - "$TOOLTIPS_FILE" <<EOF
+const fs = require('fs');
+const file = process.argv[1];
+const list = JSON.parse(fs.readFileSync(file, 'utf8'));
+const maxId = list.reduce((m, t) => Math.max(m, Number(t.id) || 0), 0);
+const newId = maxId + 1;
+list.push({ id: newId, text: $(node -e "process.stdout.write(JSON.stringify('$TOOLTIP_TEXT'))"), enabled: true });
+fs.writeFileSync('${TMP_FILE}', JSON.stringify(list, null, 2));
+console.log(newId);
+EOF
+)
+
+# Validate and move
+node -e "JSON.parse(require('fs').readFileSync('$TMP_FILE','utf8'))" 2>/dev/null \
+  || { rm -f "$TMP_FILE"; error "Generated JSON failed validation"; }
+
+mv "$TMP_FILE" "$TOOLTIPS_FILE"
+info "Added tooltip #${NEW_ID}: ${TOOLTIP_TEXT:0:60}"
+echo "$NEW_ID"
diff --git a/deploy.sh b/deploy.sh
index c08825d..ce56cf2 100755
--- a/deploy.sh
+++ b/deploy.sh
@@ -211,6 +211,24 @@ else
     exit 1
 fi
 
+# ---------------------------------------------------------
+# 3b) Auto-run tooltip generation script (must run before bot restart)
+# ---------------------------------------------------------
+say "Step 3b — Refreshing Helpful Tooltips…"
+TOOLTIP_SCRIPT="$PROJECT_DIR/generate_tooltips.sh"
+if [[ -x "$TOOLTIP_SCRIPT" ]]; then
+    if TOOLTIP_OUT=$(RUNEWAGER_DIR="$PROJECT_DIR" bash "$TOOLTIP_SCRIPT" 2>&1); then
+        say "Helpful tooltips refreshed."
+    else
+        warn "generate_tooltips.sh failed (non-fatal): $TOOLTIP_OUT"
+        # DM admin but continue deploy
+        send_admin "⚠️ generate_tooltips.sh failed during deploy: ${TOOLTIP_OUT:0:200} — continuing deploy."
+    fi
+else
+    warn "generate_tooltips.sh not found or not executable at $TOOLTIP_SCRIPT — skipping tooltip refresh."
+    send_admin "⚠️ generate_tooltips.sh missing at $TOOLTIP_SCRIPT — tooltips not refreshed."
+fi
+
 # ---------------------------------------------------------
 # 4) Start bot via systemctl
 # ---------------------------------------------------------
diff --git a/generate_tooltips.sh b/generate_tooltips.sh
new file mode 100755
index 0000000..9d03261
--- /dev/null
+++ b/generate_tooltips.sh
@@ -0,0 +1,75 @@
+#!/usr/bin/env bash
+# generate_tooltips.sh — Refresh the Helpful Tooltips data file.
+# Idempotent: safe to run on every deploy. Creates/overwrites tooltips.json
+# from the source-of-truth DEFAULT_TIPS_LIST embedded in index.js.
+# Called automatically by deploy.sh and prod-run.sh before bot restart.
+#
+# Usage:
+#   ./generate_tooltips.sh [--dry-run]
+#   --dry-run  Print what would be written without making changes.
+
+set -euo pipefail
+
+SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
+APP_DIR="${RUNEWAGER_DIR:-$SCRIPT_DIR}"
+DATA_DIR="$APP_DIR/data"
+TOOLTIPS_FILE="$DATA_DIR/tooltips.json"
+TMP_FILE="$TOOLTIPS_FILE.tmp.$$"
+
+DRY_RUN=false
+for arg in "$@"; do
+  [[ "$arg" == "--dry-run" ]] && DRY_RUN=true
+done
+
+info()  { echo "[generate_tooltips] INFO:  $*"; }
+warn()  { echo "[generate_tooltips] WARN:  $*" >&2; }
+error() { echo "[generate_tooltips] ERROR: $*" >&2; exit 1; }
+
+# Ensure data directory exists
+mkdir -p "$DATA_DIR" || error "Cannot create data dir: $DATA_DIR"
+
+# Extract DEFAULT_TIPS_LIST from index.js using Node.js
+if [[ ! -f "$APP_DIR/index.js" ]]; then
+  error "index.js not found at $APP_DIR/index.js"
+fi
+
+info "Extracting DEFAULT_TIPS_LIST from index.js..."
+TOOLTIP_JSON=$(node - <<'EOF'
+const fs = require('fs');
+const src = fs.readFileSync(process.argv[1] || 'index.js', 'utf8');
+// Execute just the DEFAULT_TIPS_LIST block and print it as JSON
+const m = src.match(/const DEFAULT_TIPS_LIST\s*=\s*(\[[\s\S]+?\]);/);
+if (!m) { process.stderr.write('DEFAULT_TIPS_LIST not found\n'); process.exit(1); }
+try {
+  // Use Function constructor for safe eval of the array literal
+  const list = (new Function('return ' + m[1]))();
+  console.log(JSON.stringify(list, null, 2));
+} catch (e) { process.stderr.write('Parse error: ' + e.message + '\n'); process.exit(1); }
+EOF
+node "$APP_DIR/index.js" --version 2>/dev/null || true
+) || {
+  # Fallback: emit a minimal valid tooltips.json with a placeholder
+  warn "Could not extract tooltips from index.js — writing placeholder."
+  TOOLTIP_JSON='[{"id":1,"text":"Helpful tooltip placeholder — configure via /tips in the bot admin.","enabled":true}]'
+}
+
+if [[ "$DRY_RUN" == "true" ]]; then
+  info "[dry-run] Would write to $TOOLTIPS_FILE:"
+  echo "$TOOLTIP_JSON"
+  exit 0
+fi
+
+# Atomic write: write to temp file, validate JSON, then move
+echo "$TOOLTIP_JSON" > "$TMP_FILE"
+
+# Validate JSON before replacing
+node -e "JSON.parse(require('fs').readFileSync('$TMP_FILE','utf8'))" 2>/dev/null || {
+  rm -f "$TMP_FILE"
+  # Write placeholder instead of failing
+  warn "Generated JSON failed validation — writing placeholder."
+  echo '[{"id":1,"text":"Helpful tooltip placeholder — configure via /tips in the bot admin.","enabled":true}]' > "$TMP_FILE"
+}
+
+mv "$TMP_FILE" "$TOOLTIPS_FILE"
+info "Helpful tooltips refreshed → $TOOLTIPS_FILE"
+info "Total entries: $(node -e "console.log(JSON.parse(require('fs').readFileSync('$TOOLTIPS_FILE','utf8')).length)")"
diff --git a/index.js b/index.js
index b24475b..46798cb 100644
--- a/index.js
+++ b/index.js
@@ -140,7 +140,7 @@ const TELEGRAM_GROUP_ID = process.env.TELEGRAM_GROUP_ID || '';
 const ANNOUNCE_CHANNEL = TELEGRAM_CHANNEL_ID;
 const BOT_PRIVACY_MODE = String(process.env.BOT_PRIVACY_MODE || process.env.BOTPRIVACYMODE || '').trim().toLowerCase();
 
-// Group chat_id for automatic Content Drops
+// Group chat_id for automatic Helpful Tooltips
 const TIPS_GROUP = process.env.TIPS_GROUP || TELEGRAM_GROUP_ID || '';
 
 // ── Images ─────────────────────────────────────────────────────────────────
@@ -314,6 +314,8 @@ const tipsStore = {
   systemEnabled: true,
   intervalHours: 4,
   targetGroup: TIPS_GROUP,
+  targetGroupTitle: null,   // human-readable name of linked group/channel
+  silentMode: true,          // always ON per spec; stored so settings panel can display it
   nextTipId: 16,
   lastSentTipId: null,
 };
@@ -538,6 +540,8 @@ const ACTION_LABELS = {
   await_sshv_danger_confirm: 'dangerous SSHV confirmation',
   await_register_chat_forward: 'chat registration forward',
   await_referral_code: 'referral code entry',
+  await_tip_link_target: 'tooltip target group/channel link',
+  await_tip_button_syntax: 'tooltip inline button definition',
 };
 
 /**
@@ -952,6 +956,8 @@ function createRuntimeStateSnapshot() {
       systemEnabled: tipsStore.systemEnabled,
       intervalHours: tipsStore.intervalHours,
       targetGroup: tipsStore.targetGroup,
+      targetGroupTitle: tipsStore.targetGroupTitle,
+      silentMode: tipsStore.silentMode,
       nextTipId: tipsStore.nextTipId,
     },
     broadcastConfigStore: {
@@ -1205,6 +1211,8 @@ function loadRuntimeState() {
     if (typeof raw.tipsStore.targetGroup === 'string' && raw.tipsStore.targetGroup) {
       tipsStore.targetGroup = raw.tipsStore.targetGroup;
     }
+    if (typeof raw.tipsStore.targetGroupTitle === 'string') tipsStore.targetGroupTitle = raw.tipsStore.targetGroupTitle;
+    if (typeof raw.tipsStore.silentMode === 'boolean') tipsStore.silentMode = raw.tipsStore.silentMode;
     if (typeof raw.tipsStore.nextTipId === 'number') tipsStore.nextTipId = raw.tipsStore.nextTipId;
   }
   tipsStore.nextTipId = Math.max(tipsStore.nextTipId, tipsStore.tips.reduce((m, t) => Math.max(m, Number(t.id) || 0), 0) + 1);
@@ -3558,7 +3566,7 @@ function adminPromoToolsKeyboard() {
     [Markup.button.callback('👀 Preview Promo', 'admin_pm_preview')],
     [Markup.button.callback('🧾 Approval Queue', 'admin_pm_queue')],
     [Markup.button.callback('📣 Announcements', 'admin_cmd_announce_start')],
-    [Markup.button.callback('💡 Content Drops', 'admin_cmd_tips_dashboard')],
+    [Markup.button.callback('💡 Helpful Tooltips', 'admin_cmd_tips_dashboard')],
     [Markup.button.callback('⬅️ Admin Dashboard', 'open_admin_dashboard')],
     [Markup.button.callback('🏠 Main Menu', 'to_main_menu'), Markup.button.callback('❌ Cancel', 'to_main_menu')],
   ]);
@@ -4085,7 +4093,7 @@ function adminMainMenuKeyboard(user) {
     ],
     [
       Markup.button.callback('📟 VPS Console (/sshv)', 'sshv_open'),
-      Markup.button.callback('💡 Content Drops', 'admin_cmd_tips_dashboard'),
+      Markup.button.callback('💡 Helpful Tooltips', 'admin_cmd_tips_dashboard'),
     ],
     [Markup.button.callback(toggleLabel, 'admin_cmd_mode_toggle')],
     [Markup.button.callback('↩ Back to User Menu', 'pamenu_back_user')],
@@ -6045,14 +6053,14 @@ function buildHelpPages(user) {
         '/unapprove_group <chat_id> — Remove group from whitelist',
         '/list_groups — List all approved groups',
         '',
-        '💡 CONTENT DROPS MANAGEMENT',
-        '/tips (or /t, /tp) — Post a content drop to the group',
-        '/tiplist — List all tips',
-        '/tipadd — Add a new tip',
-        '/tipremove — Remove a tip',
-        '/tipedit — Edit an existing tip',
-        '/tiptoggle — Enable/disable tips feature',
-        '/tipsettings — Configure content drop settings',
+        '💡 HELPFUL TOOLTIPS MANAGEMENT',
+        '/tips (or /t, /tp) — Open Helpful Tooltips Manager',
+        '/tiplist — List all tooltips',
+        '/tipadd — Add a new tooltip',
+        '/tipremove — Remove a tooltip',
+        '/tipedit — Edit an existing tooltip',
+        '/tiptoggle — Enable/disable tooltips feature',
+        '/tipsettings — Configure tooltip settings (interval, target)',
         '',
         '📊 ANALYTICS',
         '/funnel — Conversion funnel stats',
@@ -6604,8 +6612,47 @@ function gwizSummaryText(d) {
  * Start the inline giveaway wizard.
  * config = { chatId, chatTitle, startedBy }
  */
+
+/**
+ * Pre-flight safety check before starting a giveaway.
+ * Returns { ok: true } if safe to proceed, or { ok: false, reason } with a reason string.
+ * Also DMs admin with specific remediation guidance on failure.
+ */
+async function giveawayPreflightCheck(ctx, chatId) {
+  // Check 1: group/channel must be linked
+  const hasGroup = approvedGroupsStore.size > 0 || broadcastConfigStore.targetGroup;
+  if (!hasGroup) {
+    const msg = '⚠️ No valid group/channel linked. Configure in Settings → Group Linking Tools before starting a giveaway.';
+    await notifyAdmins(msg);
+    return { ok: false, reason: msg };
+  }
+
+  // Check 2: if a specific chatId is given, verify bot has post permissions
+  if (chatId && chatId !== (ctx.from && ctx.from.id)) {
+    try {
+      const botMember = await bot.telegram.getChatMember(chatId, bot.botInfo.id).catch(() => null);
+      if (botMember) {
+        const canPin = botMember.can_pin_messages || botMember.status === 'administrator';
+        if (!canPin) {
+          const chatTitle = broadcastConfigStore.targetGroupTitle || String(chatId);
+          await notifyAdmins(`⚠️ Missing pin permission in ${chatTitle}. Please grant the bot "Pin Messages" permission before starting a giveaway.`);
+          // Not a hard block — warn only; admin can proceed
+        }
+      }
+    } catch (_) {} // non-fatal — just warn
+  }
+  return { ok: true };
+}
+
 async function gwizStart(ctx, user, config) {
   clearPendingAction(user);
+  // Safety check before starting wizard
+  const targetChatId = config.chatId || (ctx.chat && ctx.chat.id);
+  const preflight = await giveawayPreflightCheck(ctx, targetChatId);
+  if (!preflight.ok) {
+    await ctx.reply(`❌ Cannot start giveaway:\n${preflight.reason}`);
+    return;
+  }
   const data = {
     chatId: config.chatId || (ctx.chat && ctx.chat.id),
     chatTitle: config.chatTitle || (ctx.chat && ctx.chat.title) || 'DM',
@@ -7660,7 +7707,7 @@ bot.action('admin_cmd_tiptest', async (ctx) => {
   if (!requireAdmin(ctx)) return;
   await ctx.answerCbQuery();
   const enabled = tipsStore.tips.filter((t) => t.enabled);
-  if (!enabled.length) { await ctx.reply('No enabled content drops to test.'); return; }
+  if (!enabled.length) { await ctx.reply('No enabled tooltips to test.'); return; }
   const pool = enabled.length > 1 && tipsStore.lastSentTipId != null
     ? enabled.filter((t) => t.id !== tipsStore.lastSentTipId)
     : enabled;
@@ -7670,9 +7717,9 @@ bot.action('admin_cmd_tiptest', async (ctx) => {
     tipsStore.lastSentTipId = tip.id;
     persistRuntimeState();
     saveHelpfulMessages();
-    await ctx.reply(`✅ Test content drop posted to ${sendResult.target} (silent).`, Markup.inlineKeyboard([[Markup.button.callback('💡 Open Content Drops Manager', 'admin_cmd_tips_dashboard')], [Markup.button.callback('⬅️ Admin Dashboard', 'open_admin_dashboard')]]));
+    await ctx.reply(`✅ Test tooltip posted to ${sendResult.target} (silent).`, Markup.inlineKeyboard([[Markup.button.callback('💡 Open Tooltips Manager', 'admin_cmd_tips_dashboard')], [Markup.button.callback('⬅️ Admin Dashboard', 'open_admin_dashboard')]]));
   } else {
-    await ctx.reply(`❌ Failed to post test content drop. ${sendResult.error ? sendResult.error.message : 'Unknown error'}\nTip: use /register_chat or forward any message from the target group/channel here to auto-register.`);
+    await ctx.reply(`❌ Failed to post test tooltip. ${sendResult.error ? sendResult.error.message : 'Unknown error'}\nUse Settings → Link Channel/Group or forward a message from the target group/channel here to auto-register.`);
   }
 });
 
@@ -8657,7 +8704,7 @@ function adminTestsToolsKeyboard() {
   return Markup.inlineKeyboard([
     [Markup.button.callback('🧪 Run TestAll', 'admin_cmd_testall'), Markup.button.callback('🎁 Test Giveaway', 'admin_cmd_testgiveaway')],
     [Markup.button.callback('🐛 View Bug Reports', 'admin_cmd_viewbugs'), Markup.button.callback('📤 Export Bugs', 'admin_cmd_exportbugs')],
-    [Markup.button.callback('✅ Resolve Bug', 'admin_cmd_resolvebug_prompt'), Markup.button.callback('🧪 Test Content Drop', 'admin_cmd_tiptest')],
+    [Markup.button.callback('✅ Resolve Bug', 'admin_cmd_resolvebug_prompt'), Markup.button.callback('💡 Test Tooltip', 'admin_cmd_tiptest')],
     [Markup.button.callback('📟 Open SSHV Console', 'sshv_open')],
     [Markup.button.callback('⬅️ Admin Dashboard', 'open_admin_dashboard')],
     [Markup.button.callback('🏠 Main Menu', 'to_main_menu'), Markup.button.callback('❌ Cancel', 'to_main_menu')],
@@ -8674,7 +8721,7 @@ Use this menu for diagnostics, bug workflows, and test sends.
 
 • TestAll = full sanity check
 • Test Giveaway = simulated giveaway flow
-• Test Content Drop = sends one random drop to current target
+• Test Tooltip = sends one random tooltip to current target
 • SSHV = VPS console tools`,
     { parse_mode: 'Markdown', ...adminTestsToolsKeyboard() },
   );
@@ -10040,12 +10087,10 @@ async function autoRegisterForwardedChatIfPresent(ctx, user) {
   const chatId = Number(fwdChat.id);
   approvedGroupsStore.add(chatId);
   tipsStore.targetGroup = String(chatId);
+  tipsStore.targetGroupTitle = fwdChat.title || null;
   broadcastConfigStore.targetGroup = String(chatId);
   persistRuntimeState();
-  await ctx.reply(`✅ Auto-registered target chat from forwarded message:
-• ${fwdChat.title || chatId} (${chatId})
-
-Content Drops + group broadcasts now use this target.`);
+  await ctx.reply(`✅ Auto-registered target chat from forwarded message:\n• ${fwdChat.title || chatId} (${chatId})\n\nHelpful Tooltips + group broadcasts will now use this target.`);
   return true;
 }
 
@@ -10187,13 +10232,11 @@ bot.on('text', async (ctx) => {
     const chatId = Number(fwdChat.id);
     approvedGroupsStore.add(chatId);
     tipsStore.targetGroup = String(chatId);
+    tipsStore.targetGroupTitle = fwdChat.title || null;
     broadcastConfigStore.targetGroup = String(chatId);
     user.pendingAction = null;
     persistRuntimeState();
-    await ctx.reply(`✅ Registered chat for broadcasts/content drops:
-• ${fwdChat.title || chatId} (${chatId})
-
-Content Drops and group broadcasts will now use this target.`);
+    await ctx.reply(`✅ Helpful Tooltips target linked:\n• ${fwdChat.title || chatId} (${chatId})\n\nHelpful Tooltips and group broadcasts will now post to this chat.\n\n✅ Bot must already be a member with send permissions.`);
     return;
   }
 
@@ -10847,7 +10890,13 @@ C = Existing User With Wager Requirement`);
   if (action.type === 'await_tip_add_text') {
     if (!requireAdmin(ctx)) return;
     if (!text) {
-      await ctx.reply('Drop text cannot be empty. Please send the tip you want to add.');
+      await ctx.reply('Tooltip text cannot be empty. Please send the tooltip content to add.');
+      return;
+    }
+    // Validate any inline button syntax before saving
+    const addParsed = parseTooltipButtons(text);
+    if (addParsed.error) {
+      await ctx.reply(`❌ Button syntax error:\n${addParsed.error}\n\nPlease fix the button syntax and try again.`);
       return;
     }
     const newTip = { id: tipsStore.nextTipId, text, enabled: true };
@@ -10856,7 +10905,8 @@ C = Existing User With Wager Requirement`);
     user.pendingAction = null;
     persistRuntimeState();
     saveHelpfulMessages();
-    await ctx.reply(`Added as Drop #${newTip.id}.`);
+    const buttonNote = addParsed.keyboard ? ' (with inline buttons)' : '';
+    await ctx.reply(`✅ Added as Tooltip #${newTip.id}${buttonNote}.`);
     return;
   }
 
@@ -10864,21 +10914,28 @@ C = Existing User With Wager Requirement`);
   if (action.type === 'await_tip_edit_text') {
     if (!requireAdmin(ctx)) return;
     if (!text) {
-      await ctx.reply('Drop text cannot be empty. Please send the updated tip text.');
+      await ctx.reply('Tooltip text cannot be empty. Please send the updated text.');
+      return;
+    }
+    // Validate any inline button syntax before saving
+    const editParsed = parseTooltipButtons(text);
+    if (editParsed.error) {
+      await ctx.reply(`❌ Button syntax error:\n${editParsed.error}\n\nPlease fix the button syntax and try again.`);
       return;
     }
     const tipId = action.data && action.data.tipId;
     const tip = tipsStore.tips.find((t) => t.id === tipId);
     if (!tip) {
       user.pendingAction = null;
-      await ctx.reply('Tip not found — it may have been removed.');
+      await ctx.reply('Tooltip not found — it may have been removed.');
       return;
     }
     tip.text = text;
     user.pendingAction = null;
     persistRuntimeState();
     saveHelpfulMessages();
-    await ctx.reply(`Drop #${tipId} updated.`);
+    const editButtonNote = editParsed.keyboard ? ' (with inline buttons)' : '';
+    await ctx.reply(`✅ Tooltip #${tipId} updated${editButtonNote}.`);
     return;
   }
 
@@ -10886,8 +10943,8 @@ C = Existing User With Wager Requirement`);
   if (action.type === 'await_tip_settings_interval') {
     if (!requireAdmin(ctx)) return;
     const hours = Number(text);
-    if (!Number.isFinite(hours) || hours <= 0) {
-      await ctx.reply('Please send a valid number of hours (e.g. `4`).', { parse_mode: 'Markdown' });
+    if (!Number.isInteger(hours) || hours <= 0) {
+      await ctx.reply('Please send a whole number of hours (e.g. `4`).', { parse_mode: 'Markdown' });
       return;
     }
     tipsStore.intervalHours = hours;
@@ -10895,7 +10952,26 @@ C = Existing User With Wager Requirement`);
     persistRuntimeState();
     saveHelpfulMessages();
     startTipsScheduler(); // re-arm with new interval
-    await ctx.reply(`✅ Tip interval updated to every ${hours} hour(s). Scheduler restarted.`);
+    await ctx.reply(`✅ Tooltip interval updated to every ${hours} hour(s). Scheduler restarted.`);
+    return;
+  }
+
+  // Tips system: await group/channel forward to link as tooltip target
+  if (action.type === 'await_tip_link_target') {
+    if (!requireAdmin(ctx)) return;
+    const fwdChat = extractForwardedChat(ctx.message || {});
+    if (!fwdChat || !fwdChat.id) {
+      await ctx.reply('Please forward a message from the target channel or group. The bot must already be a member.');
+      return;
+    }
+    const chatId = Number(fwdChat.id);
+    approvedGroupsStore.add(chatId);
+    tipsStore.targetGroup = String(chatId);
+    tipsStore.targetGroupTitle = fwdChat.title || null;
+    broadcastConfigStore.targetGroup = String(chatId);
+    user.pendingAction = null;
+    persistRuntimeState();
+    await ctx.reply(`✅ Helpful Tooltips target linked:\n• ${fwdChat.title || chatId} (${chatId})\n\nTooltips and group broadcasts will now post to this chat.`);
     return;
   }
 
@@ -11132,7 +11208,7 @@ bot.action('announce_send_channel', async (ctx) => {
 });
 
 // =========================
-// Content Drops System — scheduler + admin commands + callbacks
+// Helpful Tooltips System — scheduler + admin commands + callbacks
 // =========================
 
 /**
@@ -11188,10 +11264,20 @@ async function postTipToConfiguredTarget(tip, telegram) {
   const fallbackTarget = approvedGroupsStore.size ? Array.from(approvedGroupsStore)[0] : null;
   const candidates = [primaryTarget, fallbackTarget].filter(Boolean);
   let lastErr = null;
+
+  // Parse inline buttons from tip text if present
+  const parsed = parseTooltipButtons(String(tip.text || ''));
+  const messageText = parsed.text || String(tip.text || '');
+  const extra = {
+    parse_mode: 'HTML',
+    disable_notification: tipsStore.silentMode !== false,
+  };
+  if (parsed.keyboard) Object.assign(extra, parsed.keyboard);
+
   for (const target of candidates) {
     try {
       // eslint-disable-next-line no-await-in-loop
-      await telegram.sendMessage(target, formatTipForHtml(tip.text), { parse_mode: 'HTML', disable_notification: true });
+      await telegram.sendMessage(target, formatTipForHtml(messageText), extra);
       tipsStore.targetGroup = String(target);
       broadcastConfigStore.targetGroup = String(target);
       return { ok: true, target };
@@ -11202,6 +11288,56 @@ async function postTipToConfiguredTarget(tip, telegram) {
   return { ok: false, error: lastErr };
 }
 
+/**
+ * Parse inline button syntax from tooltip text.
+ * Syntax: [Label - https://url] && [Label2 - https://url2] = same row; new line = new row
+ * Special: [Open Bot] adds a standard "Open Bot" button to the row.
+ * Returns { text, keyboard } — text with button lines stripped, keyboard as Telegraf array or null.
+ * Returns { error } if button syntax is malformed.
+ */
+function parseTooltipButtons(rawText) {
+  const lines = rawText.split('\n');
+  const textLines = [];
+  const buttonRows = [];
+  const OPEN_BOT_URL = 'https://t.me/RuneWager_bot';
+  const BUTTON_LINE_RE = /^\[.+?\s*-\s*https?:\/\/.+?\](\s*&&\s*\[.+?\s*-\s*https?:\/\/.+?\])*$|^\[Open Bot\](\s*&&\s*\[Open Bot\])*$/i;
+
+  for (const line of lines) {
+    const trimmed = line.trim();
+    // A button row line: one or more [Label - URL] items separated by &&
+    if (/^\[.+?\](\s*&&\s*\[.+?\])*$/.test(trimmed)) {
+      const rowButtons = [];
+      const parts = trimmed.split(/\s*&&\s*/);
+      for (const part of parts) {
+        const openBotMatch = /^\[Open Bot\]$/i.test(part.trim());
+        if (openBotMatch) {
+          rowButtons.push(Markup.button.url('Open Bot', OPEN_BOT_URL));
+          continue;
+        }
+        const m = part.trim().match(/^\[(.+?)\s*-\s*(https?:\/\/\S+?)\]$/);
+        if (!m) {
+          return { error: `Invalid button syntax: ${part.trim()}\n\nExpected format: [Label - https://url]` };
+        }
+        const [, label, url] = m;
+        try {
+          new URL(url);
+        } catch (_) {
+          return { error: `Invalid URL in button: ${url}` };
+        }
+        if (!label.trim()) return { error: 'Button label cannot be empty.' };
+        rowButtons.push(Markup.button.url(label.trim(), url));
+      }
+      if (rowButtons.length > 0) buttonRows.push(rowButtons);
+    } else {
+      textLines.push(line);
+    }
+  }
+
+  const text = textLines.join('\n').trim();
+  const keyboard = buttonRows.length > 0 ? Markup.inlineKeyboard(buttonRows) : null;
+  return { text, keyboard };
+}
+
 /**
  * Start (or restart) the tips scheduler.
  * Clears any existing timer then arms a fresh one using the current interval.
@@ -11231,14 +11367,16 @@ function startTipsScheduler() {
   }, ms);
 }
 
-/** Build the Content Drops Manager dashboard keyboard */
+/** Build the Helpful Tooltips Manager keyboard */
 function tipsDashboardKeyboard() {
+  const count = tipsStore.tips.length;
   return Markup.inlineKeyboard([
-    [Markup.button.callback('➕ Add Tip', 'tips_cmd_add'), Markup.button.callback('✏️ Edit Tip', 'tips_cmd_edit')],
-    [Markup.button.callback('❌ Remove Tip', 'tips_cmd_remove'), Markup.button.callback('🔁 Toggle System', 'tips_cmd_toggle')],
-    [Markup.button.callback('📋 View All Tips', 'tips_cmd_list'), Markup.button.callback('🧪 Test Random Tip', 'tips_cmd_test')],
-    [Markup.button.callback('⚙️ Settings', 'tips_cmd_settings')],
-    [Markup.button.callback('📥 Import Batch JSON', 'tips_cmd_import_batch')],
+    [Markup.button.callback('➕ Add Tooltip', 'tips_cmd_add'), Markup.button.callback('✏️ Edit Tooltip', 'tips_cmd_edit')],
+    [Markup.button.callback('❌ Remove Tooltip', 'tips_cmd_remove'), Markup.button.callback('🔁 Toggle System', 'tips_cmd_toggle')],
+    [Markup.button.callback(`📋 Show all Helpful Tooltips (${count})`, 'tips_cmd_list')],
+    [Markup.button.callback('🧪 Test Random Tooltip', 'tips_cmd_test')],
+    [Markup.button.callback('⚙️ Helpful Tooltips Settings', 'tips_cmd_settings')],
+    [Markup.button.callback('📥 Import Tooltips (JSON)', 'tips_cmd_import_batch')],
     [Markup.button.callback('↩ Admin Menu', 'pamenu_back_admin')],
   ]);
 }
@@ -11256,12 +11394,15 @@ function tipSelectKeyboard(action) {
   return Markup.inlineKeyboard(rows);
 }
 
-/** Send (or re-send) the Content Drops Manager dashboard */
+/** Send (or re-send) the Helpful Tooltips Manager dashboard */
 async function sendTipsDashboard(ctx) {
   const total = tipsStore.tips.length;
   const enabled = tipsStore.tips.filter((t) => t.enabled).length;
   const status = tipsStore.systemEnabled ? '🟢 Enabled' : '🔴 Disabled';
-  const text = `📝 *Content Drops Manager*\n\nStatus: ${status}\nTotal Drops: ${total} (${enabled} active)\nInterval: every ${tipsStore.intervalHours}h\nTarget: ${tipsStore.targetGroup}`;
+  const targetDisplay = tipsStore.targetGroup
+    ? `${tipsStore.targetGroupTitle ? `${tipsStore.targetGroupTitle} ` : ''}(${tipsStore.targetGroup})`
+    : '⚠️ Not linked — use Settings → Link Channel/Group';
+  const text = `💡 *Helpful Tooltips Manager*\n\nStatus: ${status}\nTotal Tooltips: ${total} (${enabled} active)\nInterval: every ${tipsStore.intervalHours}h\nSilent mode: ${tipsStore.silentMode ? 'ON' : 'OFF'}\nTarget: ${targetDisplay}`;
   await replaceCallbackPanel(ctx, text, { parse_mode: 'Markdown', ...tipsDashboardKeyboard() });
 }
 
@@ -11298,11 +11439,15 @@ bot.command('tp', handleTipsCommand);
 
 bot.command('tiplist', async (ctx) => {
   if (!requireAdmin(ctx)) return;
-  const lines = ['📋 *Current Content Drops:*\n'];
+  const lines = [`📋 *Current Helpful Tooltips (${tipsStore.tips.length}):*\n`];
   for (const [idx, tip] of tipsStore.tips.entries()) {
-    const preview = tip.text.replace(/\*/g, '').slice(0, 80);
+    const preview = tip.text.replace(/\*/g, '').replace(/<[^>]+>/g, '').slice(0, 80);
     lines.push(`${idx + 1}. #${tip.id} ${tip.enabled ? '✅' : '🔇'} ${preview}${tip.text.length > 80 ? '…' : ''}`);
   }
+  const targetLabel = tipsStore.targetGroupTitle
+    ? `${tipsStore.targetGroupTitle} (${tipsStore.targetGroup})`
+    : (tipsStore.targetGroup || 'Not linked');
+  lines.push(`\n📌 Target: ${targetLabel}`);
   await ctx.reply(lines.join('\n'), { parse_mode: 'Markdown' });
 });
 
@@ -11366,8 +11511,8 @@ bot.command('tipedit', async (ctx) => {
       return;
     }
   }
-  if (!tipsStore.tips.length) { await ctx.reply('No tips to edit.'); return; }
-  await ctx.reply('Edit which tip?', tipSelectKeyboard('tip_edit_select'));
+  if (!tipsStore.tips.length) { await ctx.reply('No tooltips to edit.'); return; }
+  await ctx.reply('Edit which tooltip?', tipSelectKeyboard('tip_edit_select'));
 });
 
 bot.command('tiptoggle', async (ctx) => {
@@ -11375,14 +11520,14 @@ bot.command('tiptoggle', async (ctx) => {
   tipsStore.systemEnabled = !tipsStore.systemEnabled;
   persistRuntimeState();
   saveHelpfulMessages();
-  const status = tipsStore.systemEnabled ? '🟢 Content Drops System Enabled' : '🔴 Content Drops System Disabled';
+  const status = tipsStore.systemEnabled ? '🟢 Helpful Tooltips System Enabled' : '🔴 Helpful Tooltips System Disabled';
   await ctx.reply(status);
 });
 
 bot.command('tiptest', async (ctx) => {
   if (!requireAdmin(ctx)) return;
   const enabled = tipsStore.tips.filter((t) => t.enabled);
-  if (!enabled.length) { await ctx.reply('No enabled tips to test.'); return; }
+  if (!enabled.length) { await ctx.reply('No enabled tooltips to test.'); return; }
   const pool = enabled.length > 1 && tipsStore.lastSentTipId != null
     ? enabled.filter((t) => t.id !== tipsStore.lastSentTipId)
     : enabled;
@@ -11392,20 +11537,21 @@ bot.command('tiptest', async (ctx) => {
     tipsStore.lastSentTipId = tip.id;
     persistRuntimeState();
     saveHelpfulMessages();
-    await ctx.reply(`✅ Test tip posted to ${sendResult.target} (silent).`);
+    await ctx.reply(`✅ Test tooltip posted to ${sendResult.target} (silent).`);
   } else {
-    await ctx.reply(`❌ Failed to post test tip. ${sendResult.error ? sendResult.error.message : 'Unknown error'}
-Tip: run /register_chat and forward a message from the target group/channel.`);
+    await ctx.reply(`❌ Failed to post test tooltip. ${sendResult.error ? sendResult.error.message : 'Unknown error'}\nUse Settings → Link Channel/Group to configure the target.`);
   }
 });
 
 bot.command('tipsettings', async (ctx) => {
   if (!requireAdmin(ctx)) return;
-  const text = `⚙️ *Content Drops Settings*\n\nInterval: every ${tipsStore.intervalHours} hours\nSilent mode: Always ON\nTarget group: ${tipsStore.targetGroup}\n\nTo change the interval, reply with the number of hours (e.g. \`4\`).`;
+  const targetDisplay = tipsStore.targetGroup
+    ? `${tipsStore.targetGroupTitle ? `${tipsStore.targetGroupTitle} ` : ''}(${tipsStore.targetGroup})`
+    : '⚠️ Not linked';
+  const text = `⚙️ *Helpful Tooltips Settings*\n\nInterval: every ${tipsStore.intervalHours} hours\nSilent mode: ${tipsStore.silentMode ? 'ON ✅' : 'OFF'}\nTarget: ${targetDisplay}\n\nUse the buttons below to update settings.`;
   const user = getUser(ctx);
   clearPendingAction(user);
-  user.pendingAction = { type: 'await_tip_settings_interval' };
-  await ctx.reply(text, { parse_mode: 'Markdown' });
+  await ctx.reply(text, { parse_mode: 'Markdown', ...tipsSettingsKeyboard() });
 });
 
 // ── Tips Dashboard inline button actions ──
@@ -11415,22 +11561,29 @@ bot.action('tips_cmd_add', async (ctx) => {
   const user = getUser(ctx);
   await ctx.answerCbQuery();
   clearPendingAction(user);
-  user.pendingAction = { type: 'await_tip_add_text' };
-  await ctx.reply('Send the new tip text. HTML and Markdown are both allowed.');
+  user.pendingAction = { type: 'await_tip_add_text', createdAt: Date.now() };
+  await ctx.reply(
+    '➕ *Add Helpful Tooltip*\n\nSend the tooltip text (HTML or plain text).\n\n'
+    + 'To attach inline buttons, use the button syntax on a new line:\n'
+    + '`[Label - https://url] && [Label2 - https://url2]` = same row\n'
+    + 'New line = new row\n\n'
+    + 'To add a standard "Open Bot" button, include `[Open Bot]` on its own line.',
+    { parse_mode: 'Markdown' },
+  );
 });
 
 bot.action('tips_cmd_edit', async (ctx) => {
   if (!requireAdmin(ctx)) return;
   await ctx.answerCbQuery();
-  if (!tipsStore.tips.length) { await ctx.reply('No tips to edit.'); return; }
-  await ctx.reply('Edit which tip?', tipSelectKeyboard('tip_edit_select'));
+  if (!tipsStore.tips.length) { await ctx.reply('No tooltips to edit.'); return; }
+  await ctx.reply('Edit which tooltip?', tipSelectKeyboard('tip_edit_select'));
 });
 
 bot.action('tips_cmd_remove', async (ctx) => {
   if (!requireAdmin(ctx)) return;
   await ctx.answerCbQuery();
-  if (!tipsStore.tips.length) { await ctx.reply('No tips to remove.'); return; }
-  await ctx.reply('Remove which tip?', tipSelectKeyboard('tip_remove'));
+  if (!tipsStore.tips.length) { await ctx.reply('No tooltips to remove.'); return; }
+  await ctx.reply('Remove which tooltip?', tipSelectKeyboard('tip_remove'));
 });
 
 bot.action('tips_cmd_toggle', async (ctx) => {
@@ -11439,7 +11592,7 @@ bot.action('tips_cmd_toggle', async (ctx) => {
   tipsStore.systemEnabled = !tipsStore.systemEnabled;
   persistRuntimeState();
   saveHelpfulMessages();
-  const status = tipsStore.systemEnabled ? '🟢 Content Drops System Enabled' : '🔴 Content Drops System Disabled';
+  const status = tipsStore.systemEnabled ? '🟢 Helpful Tooltips System Enabled' : '🔴 Helpful Tooltips System Disabled';
   await ctx.reply(status);
   await sendTipsDashboard(ctx);
 });
@@ -11447,11 +11600,15 @@ bot.action('tips_cmd_toggle', async (ctx) => {
 bot.action('tips_cmd_list', async (ctx) => {
   if (!requireAdmin(ctx)) return;
   await ctx.answerCbQuery();
-  const lines = ['📋 *Current Content Drops:*\n'];
+  const lines = [`📋 *All Helpful Tooltips (${tipsStore.tips.length}):*\n`];
   for (const [idx, tip] of tipsStore.tips.entries()) {
-    const preview = tip.text.replace(/\*/g, '').slice(0, 80);
+    const preview = tip.text.replace(/\*/g, '').replace(/<[^>]+>/g, '').slice(0, 80);
     lines.push(`${idx + 1}. #${tip.id} ${tip.enabled ? '✅' : '🔇'} ${preview}${tip.text.length > 80 ? '…' : ''}`);
   }
+  const targetLabel = tipsStore.targetGroupTitle
+    ? `${tipsStore.targetGroupTitle} (${tipsStore.targetGroup})`
+    : (tipsStore.targetGroup || '⚠️ Not linked');
+  lines.push(`\n📌 Target: ${targetLabel}`);
   await ctx.reply(lines.join('\n'), { parse_mode: 'Markdown' });
 });
 
@@ -11459,7 +11616,7 @@ bot.action('tips_cmd_test', async (ctx) => {
   if (!requireAdmin(ctx)) return;
   await ctx.answerCbQuery();
   const enabled = tipsStore.tips.filter((t) => t.enabled);
-  if (!enabled.length) { await ctx.reply('No enabled tips to test.'); return; }
+  if (!enabled.length) { await ctx.reply('No enabled tooltips to test.'); return; }
   const pool = enabled.length > 1 && tipsStore.lastSentTipId != null
     ? enabled.filter((t) => t.id !== tipsStore.lastSentTipId)
     : enabled;
@@ -11469,10 +11626,9 @@ bot.action('tips_cmd_test', async (ctx) => {
     tipsStore.lastSentTipId = tip.id;
     persistRuntimeState();
     saveHelpfulMessages();
-    await ctx.reply(`✅ Test tip posted to ${sendResult.target} (silent).`);
+    await ctx.reply(`✅ Test tooltip posted to ${sendResult.target} (silent).`);
   } else {
-    await ctx.reply(`❌ Failed to post test tip. ${sendResult.error ? sendResult.error.message : 'Unknown error'}
-Tip: run /register_chat and forward a message from the target group/channel.`);
+    await ctx.reply(`❌ Failed to post test tooltip. ${sendResult.error ? sendResult.error.message : 'Unknown error'}\nUse Settings → Link Channel/Group or forward a message from the target group/channel.`);
   }
   await sendTipsDashboard(ctx);
 });
@@ -11482,18 +11638,56 @@ bot.action('tips_cmd_import_batch', async (ctx) => {
   const user = getUser(ctx);
   await ctx.answerCbQuery();
   clearPendingAction(user);
-  user.pendingAction = { type: 'await_tip_add_text' };
-  await ctx.reply('Paste a JSON array to append tips (supports plain text or HTML):\n\n/tipadd [{"text":"<b>My Tip</b>","enabled":true}]');
+  user.pendingAction = { type: 'await_tip_add_text', createdAt: Date.now() };
+  await ctx.reply('Paste a JSON array to append tooltips (supports plain text or HTML):\n\n`/tipadd [{"text":"<b>My Tooltip</b>","enabled":true}]`', { parse_mode: 'Markdown' });
 });
 
+/** Build the Helpful Tooltips Settings keyboard */
+function tipsSettingsKeyboard() {
+  return Markup.inlineKeyboard([
+    [Markup.button.callback('⏱ Change Interval', 'tips_set_interval'), Markup.button.callback('🔗 Link Channel/Group', 'tips_set_link_target')],
+    [Markup.button.callback('↩ Back to Tooltips', 'tips_settings_back')],
+  ]);
+}
+
 bot.action('tips_cmd_settings', async (ctx) => {
+  if (!requireAdmin(ctx)) return;
+  await ctx.answerCbQuery();
+  const targetDisplay = tipsStore.targetGroup
+    ? `${tipsStore.targetGroupTitle ? `${tipsStore.targetGroupTitle} ` : ''}(${tipsStore.targetGroup})`
+    : '⚠️ Not linked';
+  const text = `⚙️ *Helpful Tooltips Settings*\n\nInterval: every ${tipsStore.intervalHours} hours\nSilent mode: ${tipsStore.silentMode ? 'ON ✅' : 'OFF'}\nTarget: ${targetDisplay}\n\nUse the buttons below to update settings.`;
+  await ctx.reply(text, { parse_mode: 'Markdown', ...tipsSettingsKeyboard() });
+});
+
+bot.action('tips_settings_back', async (ctx) => {
+  if (!requireAdmin(ctx)) return;
+  await ctx.answerCbQuery();
+  await sendTipsDashboard(ctx);
+});
+
+bot.action('tips_set_interval', async (ctx) => {
   if (!requireAdmin(ctx)) return;
   await ctx.answerCbQuery();
   const user = getUser(ctx);
   clearPendingAction(user);
-  user.pendingAction = { type: 'await_tip_settings_interval' };
-  const text = `⚙️ *Content Drops Settings*\n\nInterval: every ${tipsStore.intervalHours} hours\nSilent mode: Always ON\nTarget group: ${tipsStore.targetGroup}\n\nSend the new interval in hours (e.g. \`4\`).`;
-  await ctx.reply(text, { parse_mode: 'Markdown' });
+  user.pendingAction = { type: 'await_tip_settings_interval', createdAt: Date.now() };
+  await ctx.reply(`⏱ *Change Tooltip Interval*\n\nCurrent: every ${tipsStore.intervalHours} hours\n\nSend the new interval as a whole number of hours (e.g. \`4\`).`, { parse_mode: 'Markdown' });
+});
+
+bot.action('tips_set_link_target', async (ctx) => {
+  if (!requireAdmin(ctx)) return;
+  await ctx.answerCbQuery();
+  const user = getUser(ctx);
+  clearPendingAction(user);
+  user.pendingAction = { type: 'await_tip_link_target', createdAt: Date.now() };
+  const currentDisplay = tipsStore.targetGroup
+    ? `Current: ${tipsStore.targetGroupTitle || tipsStore.targetGroup} (${tipsStore.targetGroup})`
+    : 'No target linked yet.';
+  await ctx.reply(
+    `🔗 *Link Tooltip Channel/Group*\n\n${currentDisplay}\n\nForward any message from the target channel or group here to link it.\n\n⚠️ The bot must already be a member of that channel/group with send message permissions.`,
+    { parse_mode: 'Markdown' },
+  );
 });
 
 bot.action('tips_select_cancel', async (ctx) => {
@@ -11510,11 +11704,11 @@ bot.action(/^tip_remove_(\d+)$/, async (ctx) => {
   await ctx.answerCbQuery();
   const tipId = Number(ctx.match[1]);
   const idx = tipsStore.tips.findIndex((t) => t.id === tipId);
-  if (idx === -1) { await ctx.reply('Tip not found.'); return; }
+  if (idx === -1) { await ctx.reply('Tooltip not found.'); return; }
   tipsStore.tips.splice(idx, 1);
   persistRuntimeState();
   saveHelpfulMessages();
-  await ctx.reply(`Drop #${tipId} removed.`);
+  await ctx.reply(`✅ Tooltip #${tipId} removed.`);
 });
 
 // tip_edit_select_<id>
@@ -11523,11 +11717,19 @@ bot.action(/^tip_edit_select_(\d+)$/, async (ctx) => {
   await ctx.answerCbQuery();
   const tipId = Number(ctx.match[1]);
   const tip = tipsStore.tips.find((t) => t.id === tipId);
-  if (!tip) { await ctx.reply('Tip not found.'); return; }
+  if (!tip) { await ctx.reply('Tooltip not found.'); return; }
   const user = getUser(ctx);
   clearPendingAction(user);
-  user.pendingAction = { type: 'await_tip_edit_text', data: { tipId } };
-  await ctx.reply(`Send the updated text for Drop #${tipId}.\n\nCurrent text:\n${tip.text}`);
+  user.pendingAction = { type: 'await_tip_edit_text', data: { tipId }, createdAt: Date.now() };
+  await ctx.reply(
+    `✏️ *Edit Tooltip #${tipId}*\n\nCurrent text:\n${tip.text}\n\n`
+    + 'Send the updated tooltip text.\n\n'
+    + 'To attach inline buttons, add button rows after the text:\n'
+    + '`[Label - https://url] && [Label2 - https://url2]` = same row\n'
+    + 'New line = new row\n'
+    + '`[Open Bot]` = adds standard Open Bot button.',
+    { parse_mode: 'Markdown' },
+  );
 });
 
 // tip_toggle_<id> (per-tip enable/disable, accessible from tiplist)
@@ -11540,7 +11742,7 @@ bot.action(/^tip_toggle_(\d+)$/, async (ctx) => {
   tip.enabled = !tip.enabled;
   persistRuntimeState();
   saveHelpfulMessages();
-  await ctx.reply(`Drop #${tipId} is now ${tip.enabled ? '✅ enabled' : '🔇 disabled'}.`);
+  await ctx.reply(`Tooltip #${tipId} is now ${tip.enabled ? '✅ enabled' : '🔇 disabled'}.`);
 });
 
 // =========================
@@ -12062,75 +12264,25 @@ function createGiveaway(config) {
  */
 
 async function announceGiveaway(giveaway, botUsername) {
-  const titleLine = giveaway.title ? `\n📌 *${escapeMarkdownV2(giveaway.title)}*\n` : '';
-  const minPartLine = giveaway.minParticipants > 0
-    ? `• Min participants: ${giveaway.minParticipants}\n`
-    : '';
-  const reqLines = [
-    giveaway.requireLinked ? '• Linked Runewager username ✅' : null,
-    giveaway.requireChannel ? '• Joined GambleCodez channel ✅' : null,
-    giveaway.requireGroup ? '• Joined GambleCodez group ✅' : null,
-    giveaway.requireAge ? '• Age confirmed (18+) ✅' : null,
-    giveaway.requireVerified ? '• Account confirmed ✅' : null,
-    giveaway.requirePromo ? '• Claimed promo ✅' : null,
-    giveaway.requireWalkthrough ? '• Full walkthrough ✅' : null,
-  ].filter(Boolean);
-  const reqBlock = reqLines.length > 0 ? `\n*Requirements:*\n${reqLines.join('\n')}\n` : '';
-
-  const text = [
-    `🎉 *SC Giveaway Started!*${titleLine}`,
-    `🏆 Winners: ${giveaway.maxWinners}`,
-    `💰 SC amount per winner: ${giveaway.scPerWinner}`,
-    `⏱ Countdown timer: ${giveaway.durationMinutes} min`,
-    `ℹ️ Referrals give 2× boost for 7 days`,
-    minPartLine.trim() ? minPartLine.trim() : null,
-    reqBlock.trim() ? reqBlock.trim() : null,
-    '*Helpful tips:*',
-    '• Must open bot',
-    '• Must have Runewager username linked',
-    '• Must have joined Runewager',
-    `👥 Live joined count: ${giveaway.participants.size}`,
-    `\n👇 Tap below to join before countdown ends!`,
-  ].filter(Boolean).join('\n');
-
-  // Build join button row — depends on joinSurface
-  const joinRows = [];
-  if (giveaway.joinSurface === 'group' || giveaway.joinSurface === 'both') {
-    joinRows.push(Markup.button.callback('✅ Join Here', `gw_join_${giveaway.id}`));
-  }
-  if ((giveaway.joinSurface === 'dm' || giveaway.joinSurface === 'both') && botUsername) {
-    joinRows.push(Markup.button.url('💬 Join via DM', `https://t.me/${botUsername}?start=join_gw_${giveaway.id}`));
-  }
-
-  const kb = Markup.inlineKeyboard([
-    joinRows.length > 0 ? joinRows : [Markup.button.callback('✅ Join Giveaway', `gw_join_${giveaway.id}`)],
-    [Markup.button.url('🤖 Open Bot', botUsername ? `https://t.me/${botUsername}` : LINKS.miniAppPlay)],
-    [
-      Markup.button.callback('📋 Details', `gw_details_${giveaway.id}`),
-      Markup.button.callback('🧪 My Eligibility', `gw_elig_${giveaway.id}`),
-    ],
-    [
-      Markup.button.callback('⛔ Cancel (Admin)', `gw_cancel_${giveaway.id}`),
-      Markup.button.callback('⏱ Extend (Admin)', `gw_extend_${giveaway.id}`),
-    ],
-    [
-      Markup.button.callback('👥 Edit Winners (Admin)', `gw_edit_winners_${giveaway.id}`),
-      Markup.button.callback('💠 Edit SC (Admin)', `gw_edit_sc_${giveaway.id}`),
-    ],
-  ]);
-
+  // Post giveaway-started announcement to group
+  const text = buildGiveawayAnnouncementText(giveaway, null);
+  const kb = buildGiveawayAnnouncementKeyboard(giveaway, botUsername);
   const sent = await bot.telegram.sendMessage(giveaway.chatId, text, { parse_mode: 'Markdown', ...kb });
+  giveaway.announceMsgId = sent ? sent.message_id : null;
 
-  // Attempt to pin the announcement in the group; ignore permission errors
+  // Attempt to pin the announcement in the group; notify admin if missing permission
   if (sent && (giveaway.joinSurface === 'group' || giveaway.joinSurface === 'both')) {
     try {
       await bot.telegram.pinChatMessage(giveaway.chatId, sent.message_id, { disable_notification: true });
       giveaway.pinnedMsgId = sent.message_id;
     } catch (e) {
-      await notifyAdmins(`⚠️ Failed to pin giveaway #${giveaway.id} in chat ${giveaway.chatId}: ${e.message}`);
+      await notifyAdmins(`⚠️ Missing pin permission for giveaway #${giveaway.id} in chat ${giveaway.chatId}.\nError: ${e.message}\n\nPlease grant the bot "Pin Messages" permission.`);
     }
   }
 
+  // Schedule auto-refresh at 25% intervals (re-pins after each refresh)
+  scheduleGiveawayRefresh(giveaway);
+
   // If DM surface, also send a DM join announcement to all opted-in users
   if (giveaway.joinSurface === 'dm' || giveaway.joinSurface === 'both') {
     const dmText = `${text}\n\n_Join directly here in DM:_`;
@@ -12223,6 +12375,105 @@ function resetGiveawayTimer(giveaway) {
   giveaway.endTimer = setTimeout(() => finalizeGiveaway(giveaway.id), ms);
 }
 
+/**
+ * Schedule auto-refresh of the giveaway post at 25% intervals of total duration.
+ * Edits the announcement message, updates stats and remaining time, re-pins.
+ * Spec: 10 min → refresh at 2.5m, 5m, 7.5m (final results at 10m handled by finalizeGiveaway).
+ */
+function scheduleGiveawayRefresh(giveaway) {
+  const totalMs = giveaway.durationMinutes * 60 * 1000;
+  const refreshPoints = [0.25, 0.50, 0.75]; // 25%, 50%, 75%
+  const startTime = giveaway.endTime - totalMs;
+
+  for (const fraction of refreshPoints) {
+    const fireAt = startTime + totalMs * fraction;
+    const delay = fireAt - Date.now();
+    if (delay < 1000) continue; // already past
+    const t = setTimeout(async () => {
+      if (!giveawayStore.running.has(giveaway.id)) return;
+      try {
+        const remaining = Math.max(0, giveaway.endTime - Date.now());
+        const remMins = Math.floor(remaining / 60000);
+        const remSecs = Math.floor((remaining % 60000) / 1000);
+        const remStr = remMins > 0 ? `${remMins}m ${remSecs}s` : `${remSecs}s`;
+        const refreshText = buildGiveawayAnnouncementText(giveaway, remStr);
+        const kb = buildGiveawayAnnouncementKeyboard(giveaway);
+
+        if (giveaway.announceMsgId) {
+          // Try to edit existing message (jumps to bottom in some clients)
+          await bot.telegram.editMessageText(
+            giveaway.chatId, giveaway.announceMsgId, null,
+            refreshText, { parse_mode: 'Markdown', ...kb },
+          ).catch(async () => {
+            // Edit failed — send a fresh message
+            const sent = await bot.telegram.sendMessage(giveaway.chatId, refreshText, { parse_mode: 'Markdown', ...kb });
+            giveaway.announceMsgId = sent.message_id;
+          });
+        } else {
+          const sent = await bot.telegram.sendMessage(giveaway.chatId, refreshText, { parse_mode: 'Markdown', ...kb });
+          giveaway.announceMsgId = sent.message_id;
+        }
+
+        // Re-pin after refresh
+        if (giveaway.announceMsgId && (giveaway.joinSurface === 'group' || giveaway.joinSurface === 'both')) {
+          await bot.telegram.pinChatMessage(giveaway.chatId, giveaway.announceMsgId, { disable_notification: true })
+            .catch(() => {});
+          giveaway.pinnedMsgId = giveaway.announceMsgId;
+        }
+      } catch (e) {
+        logEvent('warn', 'giveaway_refresh_failed', { gwId: giveaway.id, error: e.message });
+      }
+    }, delay);
+    giveaway.reminders.push(t);
+  }
+}
+
+/** Build the announcement text for a running giveaway (used for initial post and refreshes). */
+function buildGiveawayAnnouncementText(giveaway, remainingStr) {
+  const titleLine = giveaway.title ? `\n📌 *${escapeMarkdownV2(giveaway.title)}*\n` : '';
+  const minPartLine = giveaway.minParticipants > 0 ? `• Min participants: ${giveaway.minParticipants}\n` : '';
+  const reqLines = [
+    giveaway.requireLinked ? '• Linked Runewager username ✅' : null,
+    giveaway.requireChannel ? '• Joined GambleCodez channel ✅' : null,
+    giveaway.requireGroup ? '• Joined GambleCodez group ✅' : null,
+    giveaway.requireAge ? '• Age confirmed (18+) ✅' : null,
+    giveaway.requireVerified ? '• Account confirmed ✅' : null,
+    giveaway.requirePromo ? '• Claimed promo ✅' : null,
+    giveaway.requireWalkthrough ? '• Full walkthrough ✅' : null,
+  ].filter(Boolean);
+  const reqBlock = reqLines.length > 0 ? `\n*Requirements:*\n${reqLines.join('\n')}\n` : '';
+  const timeDisplay = remainingStr || `${giveaway.durationMinutes} min`;
+  return [
+    `🎉 *SC Giveaway!*${titleLine}`,
+    `🏆 Winners: ${giveaway.maxWinners}`,
+    `💰 SC per winner: ${giveaway.scPerWinner}`,
+    `⏱ ${remainingStr ? 'Time remaining: ' + remainingStr : 'Duration: ' + timeDisplay}`,
+    `ℹ️ Referrals give 2× boost for 7 days`,
+    minPartLine.trim() || null,
+    reqBlock.trim() || null,
+    `👥 Joined: ${giveaway.participants.size}`,
+    `\n👇 Tap below to join before countdown ends!`,
+  ].filter(Boolean).join('\n');
+}
+
+/** Build the inline keyboard for a running giveaway announcement. */
+function buildGiveawayAnnouncementKeyboard(giveaway, botUsername) {
+  const joinRows = [];
+  if (giveaway.joinSurface === 'group' || giveaway.joinSurface === 'both') {
+    joinRows.push(Markup.button.callback('✅ Join Here', `gw_join_${giveaway.id}`));
+  }
+  if ((giveaway.joinSurface === 'dm' || giveaway.joinSurface === 'both') && botUsername) {
+    joinRows.push(Markup.button.url('💬 Join via DM', `https://t.me/${botUsername}?start=join_gw_${giveaway.id}`));
+  }
+  return Markup.inlineKeyboard([
+    joinRows.length > 0 ? joinRows : [Markup.button.callback('✅ Join Giveaway', `gw_join_${giveaway.id}`)],
+    [Markup.button.url('🤖 Open Bot', botUsername ? `https://t.me/${botUsername}` : LINKS.miniAppPlay)],
+    [Markup.button.callback('📋 Details', `gw_details_${giveaway.id}`), Markup.button.callback('🧪 My Eligibility', `gw_elig_${giveaway.id}`)],
+    [Markup.button.callback('⛔ Cancel (Admin)', `gw_cancel_${giveaway.id}`), Markup.button.callback('⏱ Extend (Admin)', `gw_extend_${giveaway.id}`)],
+    [Markup.button.callback('👥 Edit Winners (Admin)', `gw_edit_winners_${giveaway.id}`), Markup.button.callback('💠 Edit SC (Admin)', `gw_edit_sc_${giveaway.id}`)],
+  ]);
+}
+
 /**
 
  * scheduleGiveawayReminders executes its scoped Runewager logic and participates in menu/command or utility flow composition.
@@ -12244,18 +12495,37 @@ function resetGiveawayTimer(giveaway) {
  */
 
 function scheduleGiveawayReminders(giveaway) {
-  const points = [10, 5, 1];
-  points.forEach((m) => {
-    const at = giveaway.endTime - m * 60 * 1000;
-    const delay = at - Date.now();
-    if (delay > 1000) {
-      const t = setTimeout(async () => {
-        if (!giveawayStore.running.has(giveaway.id)) return;
-        await bot.telegram.sendMessage(giveaway.chatId, `⏳ Giveaway #${giveaway.id}: ${m} minute(s) remaining.`);
-      }, delay);
-      giveaway.reminders.push(t);
-    }
-  });
+  const scheduleReminder = (delayMs, getMessage) => {
+    if (delayMs < 500) return;
+    const t = setTimeout(async () => {
+      if (!giveawayStore.running.has(giveaway.id)) return;
+      try {
+        await bot.telegram.sendMessage(giveaway.chatId, getMessage());
+      } catch (_) {}
+    }, delayMs);
+    giveaway.reminders.push(t);
+  };
+
+  // Minute-based checkpoints: 10, 5 min
+  for (const m of [10, 5]) {
+    const delay = giveaway.endTime - m * 60 * 1000 - Date.now();
+    scheduleReminder(delay, () => `⏳ Giveaway #${giveaway.id}: ${m} minutes remaining!`);
+  }
+
+  // 1 minute remaining
+  scheduleReminder(giveaway.endTime - 60 * 1000 - Date.now(),
+    () => `⏰ 1 minute remaining! Last chance to join Giveaway #${giveaway.id}!`);
+
+  // 30 seconds remaining
+  scheduleReminder(giveaway.endTime - 30 * 1000 - Date.now(),
+    () => `⏰ 30 seconds remaining! Giveaway #${giveaway.id} ends very soon!`);
+
+  // 10-second countdown: 10, 9, 8, ... 1
+  for (let sec = 10; sec >= 1; sec--) {
+    const delay = giveaway.endTime - sec * 1000 - Date.now();
+    const s = sec; // capture
+    scheduleReminder(delay, () => `⏳ ${s}...`);
+  }
 }
 
 /**
@@ -12361,9 +12631,10 @@ async function finalizeGiveaway(gwId, forceEnd = false) {
   giveaway.winners = selected;
 
   if (!giveaway.dryRun) {
-    await bot.telegram.sendMessage(giveaway.chatId, renderWinnersText(giveaway)).catch(() => {});
+    await bot.telegram.sendMessage(giveaway.chatId, renderWinnersText(giveaway), { parse_mode: 'HTML' }).catch(() => {});
   }
 
+  const dmFailedUsers = [];
   for (const winner of giveaway.winners) {
     try {
       // Apply 2× SC boost if the winner has an active referral boost
@@ -12372,25 +12643,52 @@ async function finalizeGiveaway(gwId, forceEnd = false) {
       const awardedSc = hasBoostedPrize ? giveaway.scPerWinner * 2 : giveaway.scPerWinner;
       winner.awardedSc = awardedSc;
       winner.boosted = hasBoostedPrize;
+      winner.rwUsername = (winnerUser && winnerUser.runewagerUsername) || winner.runewagerUsername || '';
       // eslint-disable-next-line no-await-in-loop
       await bot.telegram.sendMessage(
         winner.userId,
-        `🎉 You won Giveaway #${giveaway.id}!\n`
-        + `Prize: ${awardedSc} SC${hasBoostedPrize ? ' 🔥 (2× Referral Boost applied!)' : ''}\n`
-        + `Runewager username on file: ${winner.runewagerUsername || '(not linked)'}\n`
-        + `Admin will handle prize distribution.`,
+        `🎉 *You won Giveaway #${giveaway.id}!*\n\n`
+        + `Prize: *${awardedSc} SC*${hasBoostedPrize ? ' 🔥 (2× Referral Boost applied!)' : ''}\n`
+        + `Runewager username on file: \`${winner.rwUsername || 'not linked'}\`\n\n`
+        + `ℹ️ The bot will DM you automatically once your tip has been sent. Please allow up to 24 hours for processing.`,
+        { parse_mode: 'Markdown' },
       );
     } catch (_) {
-      // ignore DM failures (user may have blocked bot)
+      // DM failed — log for admin report
+      dmFailedUsers.push(winner.userId);
     }
   }
 
-  const winnerLines = giveaway.winners.map((w) =>
-    `• ${w.tgUsername ? '@' + w.tgUsername : w.firstName || 'User'} — ${w.awardedSc || giveaway.scPerWinner} SC${w.boosted ? ' 🔥 boosted' : ''}`
-  ).join('\n');
-  await notifyAdmins(
-    `📊 Giveaway Report #${giveaway.id}\nChat ID: ${giveaway.chatId}\nBase SC each: ${giveaway.scPerWinner}\nTotal participants: ${eligibleCount}\nWinners:\n${winnerLines}\n\nAdmin actions:\n- Reroll: /admin then callback gw_reroll_${giveaway.id}\n- Mark paid: callback gw_paid_${giveaway.id}\n- Export: callback gw_export_${giveaway.id}`,
-  );
+  // Full admin report per spec item 10
+  const winnerDetailLines = giveaway.winners.map((w, i) => {
+    const handle = w.tgUsername ? `@${w.tgUsername}` : '(no handle)';
+    const name = w.firstName || '(no name)';
+    const rw = w.rwUsername || '(not linked)';
+    const sc = w.awardedSc || giveaway.scPerWinner;
+    const boost = w.boosted ? ' 🔥 2x boost' : '';
+    return `${i + 1}. TG: ${handle} | Name: ${name} | RW: ${rw} | Prize: ${sc} SC${boost}`;
+  }).join('\n');
+
+  const dmFailNote = dmFailedUsers.length > 0
+    ? `\n⚠️ DM failed for ${dmFailedUsers.length} winner(s): ${dmFailedUsers.join(', ')} (may have blocked bot)`
+    : '\n✅ All winner DMs delivered.';
+
+  for (const adminId of ADMIN_IDS) {
+    try {
+      // eslint-disable-next-line no-await-in-loop
+      await bot.telegram.sendMessage(
+        adminId,
+        `📊 *Giveaway #${giveaway.id} — Final Report*\n\nChat ID: \`${giveaway.chatId}\`\nBase SC each: ${giveaway.scPerWinner}\nTotal participants: ${eligibleCount}\nWinners: ${giveaway.winners.length}\n\n${winnerDetailLines}${dmFailNote}\n\nAdmin actions:\n/gw_reroll_${giveaway.id} — Reroll\n/gw_paid_${giveaway.id} — Mark paid\n/gw_export_${giveaway.id} — Export`,
+        {
+          parse_mode: 'Markdown',
+          ...Markup.inlineKeyboard([
+            [Markup.button.url('👀 View Results in Group', `https://t.me/c/${String(giveaway.chatId).replace('-100', '')}/${giveaway.announceMsgId || ''}`)],
+            [Markup.button.callback('🔄 Reroll', `gw_reroll_${giveaway.id}`), Markup.button.callback('✅ Mark Paid', `gw_paid_${giveaway.id}`)],
+          ]),
+        },
+      );
+    } catch (_) {}
+  }
 }
 
 /**
@@ -12473,7 +12771,14 @@ function renderWinnersList(winners) {
  */
 
 function renderWinnersText(giveaway) {
-  return `🎉 Giveaway ended!\nWinners (${giveaway.scPerWinner} SC each):\n${renderWinnersList(giveaway.winners)}\n\nAdmin will handle prize distribution.`;
+  // HTML format per spec item 9
+  const winnerLines = (giveaway.winners || []).map((w) => {
+    const handle = w.tgUsername ? `@${escapeHtml(w.tgUsername)}` : escapeHtml(w.firstName || 'Winner');
+    const sc = w.awardedSc || giveaway.scPerWinner;
+    const boost = w.boosted ? ' <i>(2x boost applied)</i>' : '';
+    return `• ${handle} — <b>${sc} SC</b>${boost}`;
+  }).join('\n');
+  return `🎉 <b>Giveaway Results!</b>\n\nWinners:\n${winnerLines}\n\n<i>The bot will DM you automatically once your tip has been sent.</i>`;
 }
 
 /**
@@ -13296,6 +13601,38 @@ bot.command('testall', async (ctx) => {
   if (approvedGroupsStore && typeof approvedGroupsStore.size === 'number') pass('Database Checks', 'linked_groups_store_readable');
   else fail('Database Checks', 'linked_groups_store_readable', 'approvedGroupsStore unreadable');
 
+  // ── 11. Helpful Tooltips System ──────────────────────────────────────────
+  if (typeof tipsStore === 'object' && Array.isArray(tipsStore.tips)) pass('Helpful Tooltips', 'tipsStore_shape');
+  else fail('Helpful Tooltips', 'tipsStore_shape', 'tipsStore is missing or malformed');
+  if (tipsStore.tips.length > 0) pass('Helpful Tooltips', `tooltips_loaded (${tipsStore.tips.length})`);
+  else fail('Helpful Tooltips', 'tooltips_loaded', 'No tooltips in tipsStore.tips');
+  if (typeof tipsStore.intervalHours === 'number' && tipsStore.intervalHours > 0) pass('Helpful Tooltips', `interval_hours (${tipsStore.intervalHours}h)`);
+  else fail('Helpful Tooltips', 'interval_hours', `Invalid interval: ${tipsStore.intervalHours}`);
+  if (tipsStore.targetGroup) pass('Helpful Tooltips', `target_linked (${tipsStore.targetGroupTitle || tipsStore.targetGroup})`);
+  else warn('Helpful Tooltips', 'target_linked', '⚠️ No target group/channel linked — use Settings → Link Channel/Group');
+  if (typeof parseTooltipButtons === 'function') pass('Helpful Tooltips', 'parseTooltipButtons_defined');
+  else fail('Helpful Tooltips', 'parseTooltipButtons_defined', 'parseTooltipButtons helper missing');
+  // Validate button parser with a sample
+  try {
+    const pb = parseTooltipButtons('Test text\n[Label - https://example.com]');
+    if (pb.keyboard && pb.text === 'Test text') pass('Helpful Tooltips', 'button_parser_valid');
+    else throw new Error(`unexpected result: text="${pb.text}" keyboard=${!!pb.keyboard}`);
+  } catch (e) { fail('Helpful Tooltips', 'button_parser_valid', e.message); }
+  // Validate Open Bot button syntax
+  try {
+    const pbOB = parseTooltipButtons('Test\n[Open Bot]');
+    if (pbOB.keyboard) pass('Helpful Tooltips', 'open_bot_button_syntax');
+    else throw new Error('Open Bot button not parsed');
+  } catch (e) { fail('Helpful Tooltips', 'open_bot_button_syntax', e.message); }
+
+  // ── 12. Giveaway System Extended ────────────────────────────────────────
+  if (typeof buildGiveawayAnnouncementText === 'function') pass('Giveaway System', 'buildGiveawayAnnouncementText_defined');
+  else fail('Giveaway System', 'buildGiveawayAnnouncementText_defined', 'Missing helper');
+  if (typeof scheduleGiveawayRefresh === 'function') pass('Giveaway System', 'scheduleGiveawayRefresh_defined');
+  else fail('Giveaway System', 'scheduleGiveawayRefresh_defined', 'Missing 25% refresh scheduler');
+  if (typeof giveawayPreflightCheck === 'function') pass('Giveaway System', 'preflight_check_defined');
+  else fail('Giveaway System', 'preflight_check_defined', 'Missing preflight safety check');
+
   if (!process.env.HTTPS_KEY_PATH || !process.env.HTTPS_CERT_PATH) warn('Environment Checks', 'https_paths_optional', 'HTTPS cert/key not set (HTTP mode expected).');
   else {
     try {
@@ -13966,7 +14303,7 @@ bot.command('verify_bot_setup', safeAdminHandler('verify_bot_setup', { usage: '/
     `Can read all group messages: ${me.can_read_all_group_messages ? 'YES' : 'NO'} (BotFather privacy mode affects this)`,
     `Supports inline queries: ${me.supports_inline_queries ? 'YES' : 'NO'}`,
     `Announce channel target: ${broadcastConfigStore.targetChannel}`,
-    `Content Drops/broadcast group target: ${broadcastConfigStore.targetGroup}`,
+    `Helpful Tooltips/broadcast group target: ${broadcastConfigStore.targetGroup}`,
     `Approved broadcast/group chats tracked: ${approvedGroupsStore.size}`,
   ];
   await ctx.reply(`🤖 *Bot Setup Verification*\n\n${checks.join('\n')}\n\nIf group visibility is limited, disable privacy mode in @BotFather and ensure admin rights in each target chat.`, { parse_mode: 'Markdown' });
diff --git a/prod-run.sh b/prod-run.sh
index 8eaee7b..a768a75 100755
--- a/prod-run.sh
+++ b/prod-run.sh
@@ -259,6 +259,28 @@ else
     npm install --omit=dev
 fi
 
+# ---------------------------------------------------------
+# 6b) Auto-run tooltip generation (must run before bot restart)
+say "Refreshing Helpful Tooltips..."
+TOOLTIP_SCRIPT="$PROJECT_DIR/generate_tooltips.sh"
+if [[ -x "$TOOLTIP_SCRIPT" ]]; then
+    if RUNEWAGER_DIR="$PROJECT_DIR" bash "$TOOLTIP_SCRIPT" >> /tmp/runewager-deploy.log 2>&1; then
+        say "Helpful tooltips refreshed."
+    else
+        warn "generate_tooltips.sh failed (non-fatal) — check /tmp/runewager-deploy.log"
+        # Attempt DM admin notification if bot token available
+        if [[ -n "${BOT_TOKEN:-}" && -n "${ADMIN_IDS:-}" ]]; then
+            ADMIN_ID="${ADMIN_IDS%%,*}"
+            curl -s "https://api.telegram.org/bot${BOT_TOKEN}/sendMessage" \
+                -d chat_id="$ADMIN_ID" \
+                -d text="⚠️ generate_tooltips.sh failed during prod-run — tooltips may be stale." \
+                >/dev/null 2>&1 || true
+        fi
+    fi
+else
+    warn "generate_tooltips.sh not found at $TOOLTIP_SCRIPT — skipping tooltip refresh"
+fi
+
 # ---------------------------------------------------------
 # 7) Project PID detection
 get_bot_pid() { pgrep -f "node .*${PROJECT_DIR}/index\.js" | head -n 1 || true; }