diff --git a/packages/ui/src/components/message-section.tsx b/packages/ui/src/components/message-section.tsx
index 38d828ce..fe58cd8d 100644
--- a/packages/ui/src/components/message-section.tsx
+++ b/packages/ui/src/components/message-section.tsx
@@ -1,5 +1,5 @@
 import { Show, createEffect, createMemo, createSignal, onCleanup, untrack } from "solid-js"
-import { CheckSquare, Trash, X } from "lucide-solid"
+import { MoreHorizontal, Trash, X } from "lucide-solid"
 import Kbd from "./kbd"
 import MessageBlockList, { getMessageAnchorId } from "./message-block-list"
 import MessageTimeline, { buildTimelineSegments, type TimelineSegment } from "./message-timeline"
@@ -14,6 +14,9 @@ import { showAlertDialog } from "../stores/alerts"
 import { deleteMessage } from "../stores/session-actions"
 import type { InstanceMessageStore } from "../stores/message-v2/instance-store"
 import type { DeleteHoverState } from "../types/delete-hover"
+import { buildRecordDisplayData } from "../stores/message-v2/record-display-cache"
+import { getPartCharCount } from "../lib/token-utils"
+import { isMac } from "../lib/keyboard-utils"
 const SCROLL_SCOPE = "session"
 const SCROLL_SENTINEL_MARGIN_PX = 48
 const USER_SCROLL_INTENT_WINDOW_MS = 600
@@ -78,6 +81,13 @@ export default function MessageSection(props: MessageSectionProps) {
   })
 
   const handleTimelineSegmentClick = (segment: TimelineSegment) => {
+    if (selectionMode() === "tools" && segment.type !== "tool") {
+      setActiveSegmentId(segment.id)
+      if (typeof document === "undefined") return
+      const anchor = document.getElementById(getMessageAnchorId(segment.messageId))
+      anchor?.scrollIntoView({ block: "start", behavior: "smooth" })
+      return
+    }
     setLastSelectionAnchorId(segment.id)
     setActiveSegmentId(segment.id)
     if (typeof document === "undefined") return
@@ -88,17 +98,34 @@ export default function MessageSection(props: MessageSectionProps) {
   const [selectedTimelineIds, setSelectedTimelineIds] = createSignal<Set<string>>(new Set())
   const [lastSelectionAnchorId, setLastSelectionAnchorId] = createSignal<string | null>(null)
   const [expandedMessageIds, setExpandedMessageIds] = createSignal<Set<string>>(new Set())
+  const [selectionMode, setSelectionMode] = createSignal<"all" | "tools">("all")
+  const [isDeleteMenuOpen, setIsDeleteMenuOpen] = createSignal(false)
+  let deleteMenuRef: HTMLDivElement | undefined
+  let deleteMenuButtonRef: HTMLButtonElement | undefined
 
   // Build the message group for a segment.
-  // Tool calls belong to the same message as their assistant.  Only the
-  // assistant badge triggers group selection; user badges are standalone.
+  // Tool calls belong to the same assistant turn (between user messages).
+  // Only assistant badges trigger group selection; user/tool badges are standalone.
   const getAdjacentGroup = (_clickedIndex: number, segments: TimelineSegment[]): TimelineSegment[] => {
     const clicked = segments[_clickedIndex]
     if (clicked.type === "assistant") {
-      // Group = all segments from the same message (assistant + its tools).
-      // Uses messageId instead of positional adjacency to avoid cross-message
-      // overlap when tool-only messages produce no assistant segment separator.
-      return segments.filter((s) => s.messageId === clicked.messageId)
+      let currentTurn = -1
+      const turnByMessageId = new Map<string, number>()
+      for (const segment of segments) {
+        if (segment.type === "user") {
+          currentTurn += 1
+          continue
+        }
+        if (currentTurn === -1) currentTurn = 0
+        if (!turnByMessageId.has(segment.messageId)) {
+          turnByMessageId.set(segment.messageId, currentTurn)
+        }
+      }
+      const turnIndex = turnByMessageId.get(clicked.messageId)
+      if (turnIndex === undefined) {
+        return segments.filter((s) => s.messageId === clicked.messageId)
+      }
+      return segments.filter((s) => s.type !== "user" && turnByMessageId.get(s.messageId) === turnIndex)
     }
     // User, tool, and compaction segments are standalone.
     return [clicked]
@@ -111,63 +138,36 @@ export default function MessageSection(props: MessageSectionProps) {
     if (segmentIndex === -1) return
     const segment = segments[segmentIndex]
 
-    const isCurrentlySelected = selectedTimelineIds().has(id)
+    if (selectionMode() === "tools" && segment.type !== "tool") {
+      return
+    }
+
+    const selected = selectedTimelineIds()
+    const isCurrentlySelected = selected.has(id)
     const group = getAdjacentGroup(segmentIndex, segments)
     const hasToolsInGroup = group.some((s) => s.type === "tool")
-    const toolMsgIds = new Set(group.filter((s) => s.type === "tool").map((s) => s.messageId))
-    const isGroupExpanded = toolMsgIds.size > 0 && [...toolMsgIds].every((mid) => expandedMessageIds().has(mid))
+    const isGroupCandidate = segment.type === "assistant" && hasToolsInGroup
+    const selectedInGroup = isGroupCandidate
+      ? group.reduce((count, s) => (selected.has(s.id) ? count + 1 : count), 0)
+      : 0
+    const isGroupEmpty = isGroupCandidate && selectedInGroup === 0
 
-    if (!isCurrentlySelected && (segment.type === "assistant" || segment.type === "user") && hasToolsInGroup && !isGroupExpanded) {
-      // First click on a parent with sibling tools: expand + select entire group
+    if (isGroupCandidate && !isCurrentlySelected && isGroupEmpty) {
+      // Parent click: select entire group only when none are selected yet.
+      // Tool visibility is handled by isSelectionActive() in isHidden() — no
+      // expand/collapse needed.
       setSelectedTimelineIds((prev) => {
         const next = new Set(prev)
         for (const s of group) next.add(s.id)
         return next
       })
-      setExpandedMessageIds((prev) => {
-        const next = new Set(prev)
-        for (const s of group) {
-          if (s.type === "tool") next.add(s.messageId)
-        }
-        return next
-      })
     } else if (isCurrentlySelected) {
-      if ((segment.type === "assistant" || segment.type === "user") && isGroupExpanded) {
-        // Parent re-click: collapse + deselect entire group
-        const newSelected = new Set(selectedTimelineIds())
-        for (const s of group) newSelected.delete(s.id)
-        setSelectedTimelineIds(newSelected)
-        setExpandedMessageIds((prev) => {
-          const next = new Set(prev)
-          for (const s of group) {
-            if (s.type === "tool") next.delete(s.messageId)
-          }
-          return next
-        })
-      } else if (segment.type === "tool") {
-        // Individual tool deselect
-        const newSelected = new Set(selectedTimelineIds())
-        newSelected.delete(id)
-        setSelectedTimelineIds(newSelected)
-        // Collapse tool's messageId if no other selected segment needs it
-        const anyOtherSelected = group.some((s) => s.type === "tool" && s.id !== id && newSelected.has(s.id))
-        if (!anyOtherSelected) {
-          setExpandedMessageIds((prev) => {
-            const next = new Set(prev)
-            for (const s of group) {
-              if (s.type === "tool") next.delete(s.messageId)
-            }
-            return next
-          })
-        }
-      } else {
-        // Deselect just this non-tool segment
-        const newSelected = new Set(selectedTimelineIds())
-        newSelected.delete(id)
-        setSelectedTimelineIds(newSelected)
-      }
+      // Individual deselect (tool or parent). No group deselect.
+      const newSelected = new Set(selected)
+      newSelected.delete(id)
+      setSelectedTimelineIds(newSelected)
     } else {
-      // Select just this segment (tool badge or already-expanded parent)
+      // Individual select (tool badge, parent with partial group, or standalone).
       setSelectedTimelineIds((prev) => {
         const next = new Set(prev)
         next.add(id)
@@ -176,6 +176,27 @@ export default function MessageSection(props: MessageSectionProps) {
     }
   }
 
+  const handleLongPressTimelineSelection = (segment: TimelineSegment) => {
+    setLastSelectionAnchorId(segment.id)
+    const segments = timelineSegments()
+    const segmentIndex = segments.findIndex((s) => s.id === segment.id)
+    if (segmentIndex === -1) return
+
+    if (selectionMode() === "tools" && segment.type !== "tool") {
+      return
+    }
+    const group = getAdjacentGroup(segmentIndex, segments)
+    const hasToolsInGroup = group.some((s) => s.type === "tool")
+    const isGroupCandidate = segment.type === "assistant" && hasToolsInGroup
+    if (!isGroupCandidate) {
+      handleToggleTimelineSelection(segment.id)
+      return
+    }
+    const newSelected = new Set(selectedTimelineIds())
+    for (const s of group) newSelected.delete(s.id)
+    setSelectedTimelineIds(newSelected)
+  }
+
   const handleSelectRangeTimeline = (id: string) => {
     const anchorId = lastSelectionAnchorId()
     if (!anchorId) {
@@ -195,58 +216,29 @@ export default function MessageSection(props: MessageSectionProps) {
     const start = Math.min(anchorIndex, targetIndex)
     const end = Math.max(anchorIndex, targetIndex)
 
-    // Range action follows the anchor state:
-    // - If the anchor is selected → add the range (extend selection)
-    // - If the anchor is NOT selected → remove the range (extend deselection)
-    const anchorSelected = selectedTimelineIds().has(anchorId)
-
-    if (anchorSelected) {
-      // Additive: select everything in range
-      const messagesToExpand = new Set<string>()
-      setSelectedTimelineIds((prev) => {
-        const next = new Set(prev)
-        for (let i = start; i <= end; i++) {
-          next.add(segments[i].id)
-          if (segments[i].type === "tool") messagesToExpand.add(segments[i].messageId)
-        }
-        return next
-      })
-      if (messagesToExpand.size > 0) {
-        setExpandedMessageIds((prev) => {
-          const next = new Set(prev)
-          for (const msgId of messagesToExpand) next.add(msgId)
-          return next
-        })
-      }
-    } else {
-      // Subtractive: deselect everything in range
-      const messagesToCollapse = new Set<string>()
-      const newSelected = new Set(selectedTimelineIds())
-      for (let i = start; i <= end; i++) {
-        newSelected.delete(segments[i].id)
-        if (segments[i].type === "tool") messagesToCollapse.add(segments[i].messageId)
-      }
-      setSelectedTimelineIds(newSelected)
-      if (messagesToCollapse.size > 0) {
-        setExpandedMessageIds((prev) => {
-          const next = new Set(prev)
-          for (const msgId of messagesToCollapse) {
-            // Only collapse if no other selected segment still needs this message expanded
-            const stillNeeded = segments.some((s) =>
-              s.messageId === msgId && s.type === "tool" && newSelected.has(s.id)
-            )
-            if (!stillNeeded) next.delete(msgId)
-          }
-          return next
-        })
-      }
-    }
+    const rangeSegments = selectionMode() === "tools"
+      ? segments.slice(start, end + 1).filter((s) => s.type === "tool")
+      : segments.slice(start, end + 1)
+    // Range selection replaces current selection so it can grow or shrink.
+    setSelectedTimelineIds(new Set(rangeSegments.map((segment) => segment.id)))
   }
 
   const handleClearTimelineSelection = () => {
     setSelectedTimelineIds(new Set<string>())
     setLastSelectionAnchorId(null)
-    setExpandedMessageIds(new Set<string>())
+  }
+
+  const applySelectionMode = (mode: "all" | "tools") => {
+    setSelectionMode(mode)
+    if (mode !== "tools") return
+    const segments = timelineSegments()
+    const toolIds = new Set(segments.filter((segment) => segment.type === "tool").map((segment) => segment.id))
+    setSelectedTimelineIds((prev) => {
+      if (prev.size === 0) return prev
+      const next = new Set([...prev].filter((id) => toolIds.has(id)))
+      if (next.size === 0) setLastSelectionAnchorId(null)
+      return next
+    })
   }
 
   const lastAssistantIndex = createMemo(() => {
@@ -325,15 +317,27 @@ export default function MessageSection(props: MessageSectionProps) {
   const selectedTokenTotal = createMemo(() => {
     const selected = selectedForDeletion()
     if (selected.size === 0) return 0
-    // O(n) pre-pass: aggregate chars by messageId once.
-    const charsByMessageId: Record<string, number> = {}
-    for (const seg of timelineSegments()) {
-      charsByMessageId[seg.messageId] = (charsByMessageId[seg.messageId] ?? 0) + seg.totalChars
-    }
-    // O(selected.size) lookup pass.
+    // Fresh-from-store chars: read parts directly via buildRecordDisplayData +
+    // getPartCharCount so the toolbar stays consistent with the xray overlay
+    // (which also reads live from the store). Falls back to segment totalChars
+    // when no record is found (e.g. compaction segments).
+    const s = store()
     let total = 0
     for (const messageId of selected) {
-      total += Math.max(Math.round((charsByMessageId[messageId] ?? 0) / 4), 1)
+      let chars = 0
+      const record = s.getMessage(messageId)
+      if (record) {
+        const displayData = buildRecordDisplayData(props.instanceId, record)
+        for (const part of displayData.orderedParts) {
+          chars += getPartCharCount(part)
+        }
+      } else {
+        // Fallback: sum from segments (O(n) pre-pass scoped to this branch)
+        for (const seg of timelineSegments()) {
+          if (seg.messageId === messageId) chars += seg.totalChars
+        }
+      }
+      total += Math.max(Math.round(chars / 4), 1)
     }
     return total
   })
@@ -364,7 +368,6 @@ export default function MessageSection(props: MessageSectionProps) {
     setDeleteHover({ kind: "none" })
     setSelectedTimelineIds(new Set<string>())
     setLastSelectionAnchorId(null)
-    setExpandedMessageIds(new Set<string>())
   }
 
   createEffect(() => {
@@ -385,14 +388,10 @@ export default function MessageSection(props: MessageSectionProps) {
   const selectAllForDeletion = () => {
     const allMessageIds = messageIds()
     setSelectedForDeletion(new Set<string>(allMessageIds))
-    // Also select all timeline segments and expand tool groups
+    // Also select all timeline segments — tool visibility is handled by
+    // isSelectionActive() in isHidden(), no expand/collapse needed.
     const segments = timelineSegments()
     setSelectedTimelineIds(new Set(segments.map((s) => s.id)))
-    const toolMessageIds = new Set<string>()
-    for (const seg of segments) {
-      if (seg.type === "tool") toolMessageIds.add(seg.messageId)
-    }
-    setExpandedMessageIds(toolMessageIds)
   }
 
   const deleteSelectedMessages = async () => {
@@ -913,6 +912,14 @@ export default function MessageSection(props: MessageSectionProps) {
         next.forEach((segment) => seenTimelineSegmentKeys.add(makeTimelineKey(segment)))
         return next
       })
+
+      // Prune stale selection IDs: segment IDs are positional and change on rebuild.
+      setSelectedTimelineIds((prev) => {
+        if (prev.size === 0) return prev
+        const currentIds = new Set(timelineSegments().map((s) => s.id))
+        const pruned = new Set([...prev].filter((id) => currentIds.has(id)))
+        return pruned.size === prev.size ? prev : pruned
+      })
     })
   }
 
@@ -1015,6 +1022,19 @@ export default function MessageSection(props: MessageSectionProps) {
     hasRestoredScroll = true
   })
 
+  createEffect(() => {
+    if (!isDeleteMenuOpen()) return
+    if (typeof document === "undefined") return
+    const handleClick = (event: MouseEvent) => {
+      const target = event.target as Node
+      if (deleteMenuRef?.contains(target)) return
+      if (deleteMenuButtonRef?.contains(target)) return
+      setIsDeleteMenuOpen(false)
+    }
+    document.addEventListener("mousedown", handleClick)
+    onCleanup(() => document.removeEventListener("mousedown", handleClick))
+  })
+
   let previousToken: string | undefined
   createEffect(() => {
     const token = changeToken()
@@ -1148,7 +1168,15 @@ export default function MessageSection(props: MessageSectionProps) {
         data-scroll-buttons={scrollButtonsCount()}
       >
         <div class="message-stream-shell" ref={setShellElement}>
-          <div class="message-stream" ref={setContainerRef} onScroll={handleScroll} onMouseUp={handleStreamMouseUp}>
+          <div class="message-stream" ref={setContainerRef} onScroll={handleScroll} onMouseUp={handleStreamMouseUp} onClick={(e) => {
+            // Clicking anywhere inside the chat container clears selection mode.
+            // Only fires when selection is active and the click target is not an
+            // interactive element inside a message block (buttons, links, etc.).
+            if (selectedTimelineIds().size === 0) return
+            const target = e.target as HTMLElement
+            if (target.closest("button, a, input, [role='button']")) return
+            handleClearTimelineSelection()
+          }}>
             <div ref={setTopSentinel} aria-hidden="true" style={{ height: "1px" }} />
             <Show when={!props.loading && messageIds().length === 0}>
               <div class="empty-state">
@@ -1277,15 +1305,65 @@ export default function MessageSection(props: MessageSectionProps) {
                 <Trash class="w-4 h-4" aria-hidden="true" />
               </button>
 
-              <button
-                type="button"
-                class="message-delete-mode-button"
-                onClick={selectAllForDeletion}
-                title={t("messageSection.bulkDelete.selectAllTitle")}
-                aria-label={t("messageSection.bulkDelete.selectAllTitle")}
-              >
-                <CheckSquare class="w-4 h-4" aria-hidden="true" />
-              </button>
+              <div class="message-delete-mode-menu-container">
+                <button
+                  ref={(el) => {
+                    deleteMenuButtonRef = el
+                  }}
+                  type="button"
+                  class="message-delete-mode-button message-delete-mode-button--menu"
+                  onClick={() => setIsDeleteMenuOpen((prev) => !prev)}
+                  title={t("messageSection.bulkDelete.moreOptionsTitle")}
+                  aria-label={t("messageSection.bulkDelete.moreOptionsTitle")}
+                >
+                  <MoreHorizontal class="w-4 h-4" aria-hidden="true" />
+                </button>
+                <Show when={isDeleteMenuOpen()}>
+                  <div
+                    ref={(el) => {
+                      deleteMenuRef = el
+                    }}
+                    class="message-delete-mode-menu dropdown-surface"
+                  >
+                    <button
+                      type="button"
+                      class="dropdown-item"
+                      onClick={() => {
+                        selectAllForDeletion()
+                        setIsDeleteMenuOpen(false)
+                      }}
+                    >
+                      {t("messageSection.bulkDelete.selectAllTitle")}
+                    </button>
+                    <div class="message-delete-mode-menu-divider" aria-hidden="true" />
+                    <div class="message-delete-mode-menu-row">
+                      <span class="message-delete-mode-menu-label">
+                        {t("messageSection.bulkDelete.selectionModeLabel")}
+                      </span>
+                      <div class="message-delete-mode-menu-toggle">
+                        <button
+                          type="button"
+                          class="message-delete-mode-menu-toggle-button"
+                          data-mode="all"
+                          data-active={selectionMode() === "all"}
+                          onClick={() => applySelectionMode("all")}
+                        >
+                          {t("messageSection.bulkDelete.selectionModeAll")}
+                        </button>
+                        <button
+                          type="button"
+                          class="message-delete-mode-menu-toggle-button"
+                          data-mode="tools"
+                          data-active={selectionMode() === "tools"}
+                          onClick={() => applySelectionMode("tools")}
+                        >
+                          {t("messageSection.bulkDelete.selectionModeTools")}
+                        </button>
+                      </div>
+                    </div>
+                  </div>
+                </Show>
+              </div>
 
               <button
                 type="button"
@@ -1298,7 +1376,7 @@ export default function MessageSection(props: MessageSectionProps) {
               </button>
 
               <span class="message-delete-mode-hint keyboard-hints" aria-hidden="true">
-                {t("messageSection.bulkDelete.selectionHint")}
+                {t("messageSection.bulkDelete.selectionHint", { modifier: isMac() ? "Cmd" : "Ctrl" })}
               </span>
             </div>
           </Show>
@@ -1310,6 +1388,7 @@ export default function MessageSection(props: MessageSectionProps) {
               segments={timelineSegments()}
               onSegmentClick={handleTimelineSegmentClick}
               onToggleSelection={handleToggleTimelineSelection}
+              onLongPressSelection={handleLongPressTimelineSelection}
               onSelectRange={handleSelectRangeTimeline}
               onClearSelection={handleClearTimelineSelection}
               selectedIds={selectedTimelineIds}
diff --git a/packages/ui/src/components/message-timeline.tsx b/packages/ui/src/components/message-timeline.tsx
index b578fc39..f5da1ab5 100644
--- a/packages/ui/src/components/message-timeline.tsx
+++ b/packages/ui/src/components/message-timeline.tsx
@@ -5,6 +5,7 @@ import { messageStoreBus } from "../stores/message-v2/bus"
 import type { ClientPart } from "../types/message"
 import type { MessageRecord } from "../stores/message-v2/types"
 import { buildRecordDisplayData } from "../stores/message-v2/record-display-cache"
+import { getPartCharCount } from "../lib/token-utils"
 import { getToolIcon } from "./tool-call/utils"
 import { User as UserIcon, Bot as BotIcon, FoldVertical, ShieldAlert } from "lucide-solid"
 import { useI18n } from "../lib/i18n"
@@ -30,6 +31,7 @@ interface MessageTimelineProps {
   segments: TimelineSegment[]
   onSegmentClick?: (segment: TimelineSegment) => void
   onToggleSelection?: (id: string) => void
+  onLongPressSelection?: (segment: TimelineSegment) => void
   onSelectRange?: (id: string) => void
   onClearSelection?: () => void
   selectedIds?: Accessor<Set<string>>
@@ -68,67 +70,6 @@ function truncateText(value: string): string {
   return `${value.slice(0, MAX_TOOLTIP_LENGTH - 1).trimEnd()}…`
 }
 
-function getPartCharCount(part: ClientPart): number {
-  if (!part) return 0
-  let count = 0
-
-  if (typeof (part as any).text === "string") {
-    count += (part as any).text.length
-  }
-
-  if (part.type === "tool") {
-    const state = (part as any).state
-    if (state) {
-      if (state.input) {
-        try {
-          count += JSON.stringify(state.input).length
-        } catch {}
-      }
-      if (state.output) {
-        if (typeof state.output === "string") {
-          count += state.output.length
-        } else {
-          try {
-            count += JSON.stringify(state.output).length
-          } catch {}
-        }
-      }
-      if (state.metadata) {
-        for (const [key, val] of Object.entries(state.metadata)) {
-          // Skip filediff — it contains full before/after file content and
-          // would inflate the character count by 10-100x for large files.
-          if (key === "filediff") continue
-          if (typeof val === "string") {
-            count += val.length
-          } else if (val && typeof val === "object") {
-            try {
-              count += JSON.stringify(val).length
-            } catch {}
-          }
-        }
-      }
-    }
-  }
-
-  if (Array.isArray((part as any).content)) {
-    count += (part as any).content.reduce((acc: number, entry: unknown) => {
-      if (typeof entry === "string") return acc + entry.length
-      if (entry && typeof entry === "object") {
-        let entryCount = (String((entry as any).text || "")).length + (String((entry as any).value || "")).length
-        if (Array.isArray((entry as any).content)) {
-          entryCount += (entry as any).content.reduce((innerAcc: number, sub: unknown) => {
-            if (typeof sub === "string") return innerAcc + sub.length
-            return innerAcc + (String((sub as any)?.text || "")).length
-          }, 0)
-        }
-        return acc + entryCount
-      }
-      return acc
-    }, 0)
-  }
-  return count
-}
-
 function collectReasoningText(part: ClientPart): string {
   const stringifySegment = (segment: unknown): string => {
     if (typeof segment === "string") {
@@ -610,7 +551,11 @@ const MessageTimeline: Component<MessageTimelineProps> = (props) => {
 
   const getSegmentTokens = (segment: TimelineSegment): number => {
     const isExpanded = props.expandedMessageIds?.().has(segment.messageId) ?? false
-    if (!isExpanded && (segment.type === "assistant" || segment.type === "user")) {
+    // When tools are hidden (not expanded, not in selection mode), assistant/user
+    // bars show aggregate tokens for the whole message.  When tools are visible
+    // (expanded or selection mode active), each segment shows its own tokens to
+    // avoid double-counting.
+    if (!isExpanded && !isSelectionActive() && (segment.type === "assistant" || segment.type === "user")) {
       return aggregateTokensByMessageId()[segment.messageId] ?? 1
     }
     const chars = liveSegmentChars()[segment.id] ?? segment.totalChars
@@ -641,7 +586,7 @@ const MessageTimeline: Component<MessageTimelineProps> = (props) => {
   let wasLongPress = false
   let pressStartPos = { x: 0, y: 0 }
 
-  const handlePointerDown = (id: string, event: PointerEvent) => {
+  const handlePointerDown = (segment: TimelineSegment, event: PointerEvent) => {
     if (event.button !== 0) return
     wasLongPress = false
     pressStartPos = { x: event.clientX, y: event.clientY }
@@ -659,13 +604,17 @@ const MessageTimeline: Component<MessageTimelineProps> = (props) => {
         wasLongPress = true
 
         // Scroll anchoring: preserve visual position of the pressed badge.
-        const btn = buttonRefs.get(id)
+        const btn = buttonRefs.get(segment.id)
         let anchorOffset: number | null = null
         if (btn && scrollContainerRef) {
           anchorOffset = btn.offsetTop - scrollContainerRef.scrollTop
         }
 
-        props.onToggleSelection?.(id)
+        if (props.onLongPressSelection) {
+          props.onLongPressSelection(segment)
+        } else {
+          props.onToggleSelection?.(segment.id)
+        }
 
         if (anchorOffset !== null && btn && scrollContainerRef) {
           const desired = btn.offsetTop - anchorOffset
@@ -741,6 +690,25 @@ const MessageTimeline: Component<MessageTimelineProps> = (props) => {
     return { messageId: segment.messageId }
   })
 
+  // Pre-computed set of messageIds that have at least one tool segment.
+  // Used by groupRole() inside <For> to avoid O(n) .some() per segment → O(1) .has().
+  const messagesWithTools = createMemo(() => {
+    const set = new Set<string>()
+    for (const s of props.segments) {
+      if (s.type === "tool") set.add(s.messageId)
+    }
+    return set
+  })
+
+  // Pre-computed index map for session message ordering.
+  // Used by isDeleteHovered() to replace O(n) indexOf with O(1) Map.get().
+  const messageIdToSessionIndex = createMemo(() => {
+    const ids = store().getSessionMessageIds(props.sessionId)
+    const map = new Map<string, number>()
+    for (let i = 0; i < ids.length; i++) map.set(ids[i], i)
+    return map
+  })
+
   return (
     <div class="message-timeline-container">
       <div
@@ -763,11 +731,11 @@ const MessageTimeline: Component<MessageTimelineProps> = (props) => {
               }
 
               if (hover.kind === "deleteUpTo") {
-                const ids = store().getSessionMessageIds(props.sessionId)
-                const targetIndex = ids.indexOf(hover.messageId)
-                if (targetIndex === -1) return false
-                const segmentIndex = ids.indexOf(segment.messageId)
-                if (segmentIndex === -1) return false
+                const indexMap = messageIdToSessionIndex()
+                const targetIndex = indexMap.get(hover.messageId)
+                if (targetIndex === undefined) return false
+                const segmentIndex = indexMap.get(segment.messageId)
+                if (segmentIndex === undefined) return false
                 return segmentIndex >= targetIndex
               }
 
@@ -792,12 +760,7 @@ const MessageTimeline: Component<MessageTimelineProps> = (props) => {
             // assistant.  Uses messageId for correctness (not positional adjacency).
             const groupRole = (): "child" | "parent" | "none" => {
               if (segment.type === "tool") return "child"
-              if (segment.type === "assistant") {
-                const hasSiblingTools = props.segments.some(
-                  (s) => s.messageId === segment.messageId && s.type === "tool",
-                )
-                if (hasSiblingTools) return "parent"
-              }
+              if (segment.type === "assistant" && messagesWithTools().has(segment.messageId)) return "parent"
               return "none"
             }
             const isGroupStart = () => {
@@ -857,7 +820,10 @@ const MessageTimeline: Component<MessageTimelineProps> = (props) => {
                    } else if (event.ctrlKey || event.metaKey) {
                      props.onToggleSelection?.(segment.id)
                    } else if (isMultiSelectActive) {
-                     props.onClearSelection?.()
+                     // In selection mode, plain click scrolls to the message
+                     // instead of clearing. Selection is cleared by clicking
+                     // anywhere inside the chat container or pressing Esc.
+                     props.onSegmentClick?.(segment)
                    } else {
                      props.onSegmentClick?.(segment)
                    }
@@ -871,7 +837,7 @@ const MessageTimeline: Component<MessageTimelineProps> = (props) => {
                      }
                    }
                  }}
-                 onPointerDown={(e) => handlePointerDown(segment.id, e)}
+                onPointerDown={(e) => handlePointerDown(segment, e)}
                  onPointerUp={handlePointerUp}
                  onPointerCancel={handlePointerUp}
                  onPointerMove={handlePointerMove}
diff --git a/packages/ui/src/lib/i18n/messages/en/messaging.ts b/packages/ui/src/lib/i18n/messages/en/messaging.ts
index 61387314..a963c876 100644
--- a/packages/ui/src/lib/i18n/messages/en/messaging.ts
+++ b/packages/ui/src/lib/i18n/messages/en/messaging.ts
@@ -86,10 +86,14 @@ export const messagingMessages = {
   "messageSection.bulkDelete.toolbarAriaLabel": "Selected messages ({count})",
   "messageSection.bulkDelete.deleteSelectedTitle": "Delete selected messages",
   "messageSection.bulkDelete.selectAllTitle": "Select all messages",
+  "messageSection.bulkDelete.moreOptionsTitle": "More options",
+  "messageSection.bulkDelete.selectionModeLabel": "Selection",
+  "messageSection.bulkDelete.selectionModeAll": "All",
+  "messageSection.bulkDelete.selectionModeTools": "Tools only",
+  "messageSection.bulkDelete.selectionHint": "{modifier}+Click toggle · Shift+Click range · Esc clear",
   "messageSection.bulkDelete.cancelTitle": "Cancel selection",
   "messageSection.bulkDelete.failedTitle": "Delete failed",
   "messageSection.bulkDelete.failedMessage": "Failed to delete selected messages",
-  "messageSection.bulkDelete.selectionHint": "Ctrl+Click toggle \u00b7 Shift+Click range \u00b7 Esc clear",
   "messageItem.status.queued": "QUEUED",
   "messageItem.status.generating": "Generating...",
   "messageItem.status.sending": "Sending...",
diff --git a/packages/ui/src/lib/i18n/messages/es/messaging.ts b/packages/ui/src/lib/i18n/messages/es/messaging.ts
index 71164f45..b0af3b5b 100644
--- a/packages/ui/src/lib/i18n/messages/es/messaging.ts
+++ b/packages/ui/src/lib/i18n/messages/es/messaging.ts
@@ -88,10 +88,14 @@ export const messagingMessages = {
   "messageSection.bulkDelete.toolbarAriaLabel": "Mensajes seleccionados ({count})",
   "messageSection.bulkDelete.deleteSelectedTitle": "Eliminar mensajes seleccionados",
   "messageSection.bulkDelete.selectAllTitle": "Seleccionar todos los mensajes",
+  "messageSection.bulkDelete.moreOptionsTitle": "Más opciones",
+  "messageSection.bulkDelete.selectionModeLabel": "Selección",
+  "messageSection.bulkDelete.selectionModeAll": "Todo",
+  "messageSection.bulkDelete.selectionModeTools": "Solo herramientas",
+  "messageSection.bulkDelete.selectionHint": "{modifier}+Click para alternar · Shift+Click rango · Esc limpiar",
   "messageSection.bulkDelete.cancelTitle": "Cancelar selección",
   "messageSection.bulkDelete.failedTitle": "Error al eliminar",
   "messageSection.bulkDelete.failedMessage": "No se pudieron eliminar los mensajes seleccionados",
-  "messageSection.bulkDelete.selectionHint": "Ctrl+Click toggle \u00b7 Shift+Click range \u00b7 Esc clear",
   "messageItem.status.queued": "EN COLA",
   "messageItem.status.generating": "Generando...",
   "messageItem.status.sending": "Enviando...",
diff --git a/packages/ui/src/lib/i18n/messages/fr/messaging.ts b/packages/ui/src/lib/i18n/messages/fr/messaging.ts
index af806804..e7a1d2cd 100644
--- a/packages/ui/src/lib/i18n/messages/fr/messaging.ts
+++ b/packages/ui/src/lib/i18n/messages/fr/messaging.ts
@@ -88,10 +88,14 @@ export const messagingMessages = {
   "messageSection.bulkDelete.toolbarAriaLabel": "Messages sélectionnés ({count})",
   "messageSection.bulkDelete.deleteSelectedTitle": "Supprimer les messages sélectionnés",
   "messageSection.bulkDelete.selectAllTitle": "Tout sélectionner",
+  "messageSection.bulkDelete.moreOptionsTitle": "Plus d'options",
+  "messageSection.bulkDelete.selectionModeLabel": "Sélection",
+  "messageSection.bulkDelete.selectionModeAll": "Tous",
+  "messageSection.bulkDelete.selectionModeTools": "Outils uniquement",
+  "messageSection.bulkDelete.selectionHint": "{modifier}+clic pour basculer · Maj+clic pour la plage · Échap effacer",
   "messageSection.bulkDelete.cancelTitle": "Annuler la sélection",
   "messageSection.bulkDelete.failedTitle": "Échec de suppression",
   "messageSection.bulkDelete.failedMessage": "Impossible de supprimer les messages sélectionnés",
-  "messageSection.bulkDelete.selectionHint": "Ctrl+Click toggle \u00b7 Shift+Click range \u00b7 Esc clear",
   "messageItem.status.queued": "EN FILE",
   "messageItem.status.generating": "Génération...",
   "messageItem.status.sending": "Envoi...",
diff --git a/packages/ui/src/lib/i18n/messages/ja/messaging.ts b/packages/ui/src/lib/i18n/messages/ja/messaging.ts
index e7106385..2892a77a 100644
--- a/packages/ui/src/lib/i18n/messages/ja/messaging.ts
+++ b/packages/ui/src/lib/i18n/messages/ja/messaging.ts
@@ -88,10 +88,14 @@ export const messagingMessages = {
   "messageSection.bulkDelete.toolbarAriaLabel": "選択したメッセージ（{count}）",
   "messageSection.bulkDelete.deleteSelectedTitle": "選択したメッセージを削除",
   "messageSection.bulkDelete.selectAllTitle": "すべて選択",
+  "messageSection.bulkDelete.moreOptionsTitle": "その他のオプション",
+  "messageSection.bulkDelete.selectionModeLabel": "選択",
+  "messageSection.bulkDelete.selectionModeAll": "すべて",
+  "messageSection.bulkDelete.selectionModeTools": "ツールのみ",
+  "messageSection.bulkDelete.selectionHint": "{modifier}+クリックで切り替え · Shift+クリックで範囲選択 · Esc でクリア",
   "messageSection.bulkDelete.cancelTitle": "選択をキャンセル",
   "messageSection.bulkDelete.failedTitle": "削除に失敗しました",
   "messageSection.bulkDelete.failedMessage": "選択したメッセージの削除に失敗しました",
-  "messageSection.bulkDelete.selectionHint": "Ctrl+Click toggle \u00b7 Shift+Click range \u00b7 Esc clear",
   "messageItem.status.queued": "待機中",
   "messageItem.status.generating": "生成中...",
   "messageItem.status.sending": "送信中...",
diff --git a/packages/ui/src/lib/i18n/messages/ru/messaging.ts b/packages/ui/src/lib/i18n/messages/ru/messaging.ts
index f9822382..a37ef5da 100644
--- a/packages/ui/src/lib/i18n/messages/ru/messaging.ts
+++ b/packages/ui/src/lib/i18n/messages/ru/messaging.ts
@@ -88,10 +88,14 @@ export const messagingMessages = {
   "messageSection.bulkDelete.toolbarAriaLabel": "Выбранные сообщения ({count})",
   "messageSection.bulkDelete.deleteSelectedTitle": "Удалить выбранные сообщения",
   "messageSection.bulkDelete.selectAllTitle": "Выбрать все сообщения",
+  "messageSection.bulkDelete.moreOptionsTitle": "Больше настроек",
+  "messageSection.bulkDelete.selectionModeLabel": "Выбор",
+  "messageSection.bulkDelete.selectionModeAll": "Все",
+  "messageSection.bulkDelete.selectionModeTools": "Только инструменты",
+  "messageSection.bulkDelete.selectionHint": "{modifier}+клик переключить · Shift+клик диапазон · Esc очистить",
   "messageSection.bulkDelete.cancelTitle": "Отменить выбор",
   "messageSection.bulkDelete.failedTitle": "Ошибка удаления",
   "messageSection.bulkDelete.failedMessage": "Не удалось удалить выбранные сообщения",
-  "messageSection.bulkDelete.selectionHint": "Ctrl+Click toggle \u00b7 Shift+Click range \u00b7 Esc clear",
   "messageItem.status.queued": "В ОЧЕРЕДИ",
   "messageItem.status.generating": "Генерация…",
   "messageItem.status.sending": "Отправка…",
diff --git a/packages/ui/src/lib/i18n/messages/zh-Hans/messaging.ts b/packages/ui/src/lib/i18n/messages/zh-Hans/messaging.ts
index 9b582bf6..eaadffd9 100644
--- a/packages/ui/src/lib/i18n/messages/zh-Hans/messaging.ts
+++ b/packages/ui/src/lib/i18n/messages/zh-Hans/messaging.ts
@@ -88,10 +88,14 @@ export const messagingMessages = {
   "messageSection.bulkDelete.toolbarAriaLabel": "已选择的消息（{count}）",
   "messageSection.bulkDelete.deleteSelectedTitle": "删除已选择的消息",
   "messageSection.bulkDelete.selectAllTitle": "全选消息",
+  "messageSection.bulkDelete.moreOptionsTitle": "更多选项",
+  "messageSection.bulkDelete.selectionModeLabel": "选择",
+  "messageSection.bulkDelete.selectionModeAll": "全部",
+  "messageSection.bulkDelete.selectionModeTools": "仅工具",
+  "messageSection.bulkDelete.selectionHint": "{modifier}+点击切换 · Shift+点击范围 · Esc 清除",
   "messageSection.bulkDelete.cancelTitle": "取消选择",
   "messageSection.bulkDelete.failedTitle": "删除失败",
   "messageSection.bulkDelete.failedMessage": "无法删除已选择的消息",
-  "messageSection.bulkDelete.selectionHint": "Ctrl+Click toggle \u00b7 Shift+Click range \u00b7 Esc clear",
   "messageItem.status.queued": "排队中",
   "messageItem.status.generating": "正在生成...",
   "messageItem.status.sending": "正在发送...",
diff --git a/packages/ui/src/lib/token-utils.ts b/packages/ui/src/lib/token-utils.ts
new file mode 100644
index 00000000..7913830b
--- /dev/null
+++ b/packages/ui/src/lib/token-utils.ts
@@ -0,0 +1,70 @@
+import type { ClientPart } from "../types/message"
+
+/**
+ * Count the total character content of a message part.
+ *
+ * Used by both the xray histogram overlay (message-timeline) and the
+ * bulk-delete toolbar token pills (message-section) so both surfaces
+ * derive token estimates from the same logic.
+ *
+ * Skips `filediff` metadata — it contains full before/after file content
+ * and would inflate the character count by 10-100x for large files.
+ */
+export function getPartCharCount(part: ClientPart): number {
+  if (!part) return 0
+  let count = 0
+
+  if (typeof (part as any).text === "string") {
+    count += (part as any).text.length
+  }
+
+  if (part.type === "tool") {
+    const state = (part as any).state
+    if (state) {
+      if (state.input) {
+        try {
+          count += JSON.stringify(state.input).length
+        } catch {}
+      }
+      if (state.output) {
+        if (typeof state.output === "string") {
+          count += state.output.length
+        } else {
+          try {
+            count += JSON.stringify(state.output).length
+          } catch {}
+        }
+      }
+      if (state.metadata) {
+        for (const [key, val] of Object.entries(state.metadata)) {
+          if (key === "filediff") continue
+          if (typeof val === "string") {
+            count += val.length
+          } else if (val && typeof val === "object") {
+            try {
+              count += JSON.stringify(val).length
+            } catch {}
+          }
+        }
+      }
+    }
+  }
+
+  if (Array.isArray((part as any).content)) {
+    count += (part as any).content.reduce((acc: number, entry: unknown) => {
+      if (typeof entry === "string") return acc + entry.length
+      if (entry && typeof entry === "object") {
+        let entryCount = (String((entry as any).text || "")).length + (String((entry as any).value || "")).length
+        if (Array.isArray((entry as any).content)) {
+          entryCount += (entry as any).content.reduce((innerAcc: number, sub: unknown) => {
+            if (typeof sub === "string") return innerAcc + sub.length
+            return innerAcc + (String((sub as any)?.text || "")).length
+          }, 0)
+        }
+        return acc + entryCount
+      }
+      return acc
+    }, 0)
+  }
+  return count
+}
diff --git a/packages/ui/src/styles/messaging/message-selection.css b/packages/ui/src/styles/messaging/message-selection.css
index 3e535488..80a5d2cf 100644
--- a/packages/ui/src/styles/messaging/message-selection.css
+++ b/packages/ui/src/styles/messaging/message-selection.css
@@ -111,6 +111,90 @@
   color: var(--text-primary);
 }
 
+.message-delete-mode-button--menu {
+  color: var(--text-muted);
+}
+
+.message-delete-mode-button--menu:hover {
+  color: var(--text-primary);
+}
+
+.message-delete-mode-menu-container {
+  position: relative;
+}
+
+.message-delete-mode-menu {
+  right: 0;
+  bottom: calc(100% + 6px);
+  min-width: 150px;
+  width: max-content;
+  max-width: min(70vw, 220px);
+  padding: 2px 0;
+}
+
+.message-delete-mode-menu-divider {
+  height: 1px;
+  margin: 3px 0;
+  background-color: var(--border-base);
+}
+
+.message-delete-mode-menu-row {
+  display: flex;
+  flex-direction: column;
+  gap: 3px;
+  padding: 2px 8px 6px;
+}
+
+.message-delete-mode-menu-label {
+  font-size: 12px;
+  color: var(--text-muted);
+  text-align: center;
+}
+
+.message-delete-mode-menu-toggle {
+  display: inline-flex;
+  border-radius: 999px;
+  border: 1px solid var(--border-base);
+  background-color: var(--surface-secondary);
+  overflow: hidden;
+  width: 100%;
+}
+
+.message-delete-mode-menu-toggle-button {
+  padding: 2px 8px;
+  font-size: 12px;
+  color: var(--text-muted);
+  background: transparent;
+  border: none;
+  cursor: pointer;
+  transition: color 0.15s ease, background-color 0.15s ease;
+}
+
+.message-delete-mode-menu-toggle-button[data-mode="all"] {
+  flex: 0 0 auto;
+  min-width: 56px;
+}
+
+.message-delete-mode-menu-toggle-button[data-mode="tools"] {
+  flex: 1 1 auto;
+}
+
+.message-delete-mode-menu-toggle-button[data-active="true"] {
+  color: var(--text-primary);
+  background-color: color-mix(in oklab, var(--accent-primary) 18%, transparent);
+}
+
+.message-delete-mode-menu .dropdown-item {
+  width: calc(100% - 8px);
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  margin: 0 4px;
+  padding: 3px 8px;
+  font-size: 12px;
+  border-radius: 6px;
+}
+
 .message-delete-mode-button:focus-visible {
   outline: none;
   box-shadow: 0 0 0 2px color-mix(in oklab, var(--accent-primary) 45%, transparent);
diff --git a/packages/ui/src/styles/messaging/message-timeline.css b/packages/ui/src/styles/messaging/message-timeline.css
index 2faeba52..5c11fce2 100644
--- a/packages/ui/src/styles/messaging/message-timeline.css
+++ b/packages/ui/src/styles/messaging/message-timeline.css
@@ -357,10 +357,10 @@
   font-weight: 600;
   font-variant-numeric: tabular-nums;
   line-height: 1;
-  color: #1a1a2e;
-  background: #ffffff;
+  color: var(--text-primary);
+  background: var(--surface-base);
   padding: 1px 5px;
-  border: 1px solid #1a1a2e;
+  border: 1px solid var(--border-base);
   border-radius: 999px;
   white-space: nowrap;
   pointer-events: none;