diff --git a/packages/kilo-vscode/src/agent-manager/AgentManagerProvider.ts b/packages/kilo-vscode/src/agent-manager/AgentManagerProvider.ts
index 6b78625095..5437543cb1 100644
--- a/packages/kilo-vscode/src/agent-manager/AgentManagerProvider.ts
+++ b/packages/kilo-vscode/src/agent-manager/AgentManagerProvider.ts
@@ -1543,6 +1543,16 @@ export class AgentManagerProvider implements Disposable {
     await this.onCreateWorktree(baseBranch, branchName)
   }
 
+  public async openAdvancedWorktree(): Promise<void> {
+    this.openPanel()
+    const panel = this.panel
+    if (!panel) return
+    await panel.waitForActive()
+    await panel.waitForReady()
+    await this.waitForStateReady("openAdvancedWorktree")
+    queueMicrotask(() => this.postToWebview({ type: "action", action: "advancedWorktree" }))
+  }
+
   private handleSection(m: AgentManagerInMessage): boolean {
     return handleSection(this.state, m, () => this.pushState())
   }
diff --git a/packages/kilo-vscode/src/agent-manager/host.ts b/packages/kilo-vscode/src/agent-manager/host.ts
index 1f86425194..92970ecac7 100644
--- a/packages/kilo-vscode/src/agent-manager/host.ts
+++ b/packages/kilo-vscode/src/agent-manager/host.ts
@@ -56,6 +56,12 @@ export interface PanelContext {
   /** Send a message to the webview. */
   postMessage(msg: unknown): void
 
+  /** Resolve once the panel webview is ready to receive messages. */
+  waitForReady(): Promise<void>
+
+  /** Resolve once the panel is the active editor tab. */
+  waitForActive(): Promise<void>
+
   /** Reveal the panel. */
   reveal(preserveFocus?: boolean): void
 
diff --git a/packages/kilo-vscode/src/agent-manager/vscode-host.ts b/packages/kilo-vscode/src/agent-manager/vscode-host.ts
index 06370eae2f..8b5ebfdc72 100644
--- a/packages/kilo-vscode/src/agent-manager/vscode-host.ts
+++ b/packages/kilo-vscode/src/agent-manager/vscode-host.ts
@@ -110,6 +110,19 @@ export class VscodeHost implements Host {
       postMessage(msg) {
         void panel.webview.postMessage(msg)
       },
+      waitForReady() {
+        return provider.waitForReady()
+      },
+      waitForActive() {
+        if (panel.active) return Promise.resolve()
+        return new Promise((resolve) => {
+          const sub = panel.onDidChangeViewState((e) => {
+            if (!e.webviewPanel.active) return
+            sub.dispose()
+            resolve()
+          })
+        })
+      },
       reveal(preserveFocus) {
         panel.reveal(vscode.ViewColumn.One, preserveFocus ?? false)
       },
diff --git a/packages/kilo-vscode/src/extension.ts b/packages/kilo-vscode/src/extension.ts
index 2b6f5e8ba3..a6f4905c31 100644
--- a/packages/kilo-vscode/src/extension.ts
+++ b/packages/kilo-vscode/src/extension.ts
@@ -338,9 +338,9 @@ export function activate(context: vscode.ExtensionContext) {
     vscode.commands.registerCommand("kilo-code.new.agentManager.closeWorktree", () => {
       agentManagerProvider.postMessage({ type: "action", action: "closeWorktree" })
     }),
-    vscode.commands.registerCommand("kilo-code.new.agentManager.advancedWorktree", () => {
-      agentManagerProvider.postMessage({ type: "action", action: "advancedWorktree" })
-    }),
+    vscode.commands.registerCommand("kilo-code.new.agentManager.advancedWorktree", () =>
+      agentManagerProvider.openAdvancedWorktree(),
+    ),
     ...Array.from({ length: 9 }, (_, i) =>
       vscode.commands.registerCommand(`kilo-code.new.agentManager.jumpTo${i + 1}`, () => {
         agentManagerProvider.postMessage({ type: "action", action: `jumpTo${i + 1}` })
diff --git a/packages/kilo-vscode/webview-ui/agent-manager/AgentManagerApp.tsx b/packages/kilo-vscode/webview-ui/agent-manager/AgentManagerApp.tsx
index 401be6510a..4239f4e735 100644
--- a/packages/kilo-vscode/webview-ui/agent-manager/AgentManagerApp.tsx
+++ b/packages/kilo-vscode/webview-ui/agent-manager/AgentManagerApp.tsx
@@ -1,7 +1,8 @@
 // Agent Manager root component
 
+/** @jsxImportSource solid-js */
+
 import {
-  Component,
   For,
   Show,
   createSignal,
@@ -11,6 +12,7 @@ import {
   onMount,
   onCleanup,
   type Accessor,
+  type Component,
 } from "solid-js"
 import type {
   ExtensionMessage,
@@ -2285,7 +2287,7 @@ const AgentManagerContent: Component = () => {
                         <DropdownMenu.Separator />
                         <DropdownMenu.Item onSelect={showAdvancedWorktreeDialog}>
                           <Icon name="settings-gear" size="small" />
-                          <DropdownMenu.ItemLabel>{t("agentManager.dialog.advanced")}</DropdownMenu.ItemLabel>
+                          <DropdownMenu.ItemLabel>{t("agentManager.dialog.configureWorktree")}</DropdownMenu.ItemLabel>
                           <span class="am-menu-shortcut">
                             {parseBindingTokens(kb().advancedWorktree ?? "").map((token) => (
                               <kbd class="am-menu-key">{token}</kbd>
diff --git a/packages/kilo-vscode/webview-ui/agent-manager/NewWorktreeDialog.tsx b/packages/kilo-vscode/webview-ui/agent-manager/NewWorktreeDialog.tsx
index 13f5692bf6..3e54451f4e 100644
--- a/packages/kilo-vscode/webview-ui/agent-manager/NewWorktreeDialog.tsx
+++ b/packages/kilo-vscode/webview-ui/agent-manager/NewWorktreeDialog.tsx
@@ -1,6 +1,8 @@
 // New Worktree dialog — prompt, versions, model, mode, import tab
 
-import { Component, For, Show, createSignal, createEffect, createMemo, onMount, onCleanup } from "solid-js"
+/** @jsxImportSource solid-js */
+
+import { type Component, For, Show, createSignal, createEffect, createMemo, onMount, onCleanup } from "solid-js"
 import type { AgentManagerBranchesMessage, AgentManagerImportResultMessage, BranchInfo } from "../src/types/messages"
 import { Dialog } from "@kilocode/kilo-ui/dialog"
 import { showToast } from "@kilocode/kilo-ui/toast"
@@ -171,6 +173,17 @@ export const NewWorktreeDialog: Component<{ onClose: () => void; defaultBaseBran
     vscode.postMessage({ type: "agentManager.requestBranches" })
     // Resize textarea if restoring a cached prompt
     if (prompt()) adjustHeight()
+    const focus = () => {
+      textareaRef?.focus({ preventScroll: true })
+      const end = textareaRef?.value.length ?? 0
+      textareaRef?.setSelectionRange(end, end)
+    }
+    requestAnimationFrame(() => {
+      focus()
+      requestAnimationFrame(focus)
+      setTimeout(focus, 0)
+      setTimeout(focus, 50)
+    })
   })
 
   const effectiveBaseBranch = () => baseBranch() ?? defaultBranch()
diff --git a/packages/kilo-vscode/webview-ui/agent-manager/i18n/en.ts b/packages/kilo-vscode/webview-ui/agent-manager/i18n/en.ts
index bde300bd16..e564072f3a 100644
--- a/packages/kilo-vscode/webview-ui/agent-manager/i18n/en.ts
+++ b/packages/kilo-vscode/webview-ui/agent-manager/i18n/en.ts
@@ -77,7 +77,7 @@ export const dict = {
   "agentManager.shortcuts.nextItem": "Next item",
   "agentManager.shortcuts.newWorktree": "New worktree",
   "agentManager.shortcuts.openWorktree": "Open worktree",
-  "agentManager.shortcuts.advancedWorktree": "Advanced worktree",
+  "agentManager.shortcuts.advancedWorktree": "Configure new worktree",
   "agentManager.shortcuts.deleteWorktree": "Delete worktree",
   "agentManager.shortcuts.previousTab": "Previous tab",
   "agentManager.shortcuts.nextTab": "Next tab",
@@ -122,6 +122,7 @@ export const dict = {
   "agentManager.dialog.createWorktree": "Create Worktree",
   "agentManager.dialog.removeImage": "Remove image",
   "agentManager.dialog.advanced": "Advanced...",
+  "agentManager.dialog.configureWorktree": "Configure New Worktree...",
 
   "agentManager.diff.toggle": "Toggle diff",
   "agentManager.diff.openFile": "Open file",
diff --git a/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx b/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx
index dbf4cea2a9..819b95eaa3 100644
--- a/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx
+++ b/packages/kilo-vscode/webview-ui/src/components/chat/ChatView.tsx
@@ -54,6 +54,7 @@ export const ChatView: Component<ChatViewProps> = (props) => {
   const [transferring, setTransferring] = createSignal(false)
   const [transferDetail, setTransferDetail] = createSignal("")
   const [repoBranch, setRepoBranch] = createSignal<string>()
+  let worktreeRef: HTMLDivElement | undefined
 
   // Permissions and questions scoped to this session's family (self + subagents).
   // Each ChatView only sees its own session tree — no cross-session leakage.
@@ -146,7 +147,10 @@ export const ChatView: Component<ChatViewProps> = (props) => {
 
   const openAgentManager = () => vscode.postMessage({ type: "openAgentManager" })
 
+  const openChanges = () => vscode.postMessage({ type: "openChanges" })
+
   const moveToWorktree = () => {
+    if (transferring()) return
     const sid = id()
     if (!sid) return
     setTransferring(true)
@@ -159,6 +163,19 @@ export const ChatView: Component<ChatViewProps> = (props) => {
 
   const advancedTooltip = "Open the Agent Manager worktree dialog to configure a new worktree before creating it."
 
+  const moveTooltip = () => {
+    const stats = session.worktreeStats()
+    if (!stats?.files)
+      return "Move this conversation and your current local changes into a dedicated worktree for isolated follow-up work."
+    return `Move this conversation and ${stats.files} changed file${stats.files > 1 ? "s" : ""} into a dedicated worktree for isolated follow-up work.`
+  }
+
+  const changesTooltip = () => {
+    const stats = session.worktreeStats()
+    if (!stats?.files) return "Open the changes view to inspect the current working tree."
+    return `${stats.files} file${stats.files > 1 ? "s" : ""} changed · +${stats.additions} -${stats.deletions}. Open the changes view.`
+  }
+
   const showAdvancedWorktree = () => vscode.postMessage({ type: "openAdvancedWorktree" })
 
   createEffect(() => {
@@ -169,13 +186,27 @@ export const ChatView: Component<ChatViewProps> = (props) => {
   const renderActions = (hasChat: boolean) => (
     <div class="new-task-button-wrapper" classList={{ "new-task-button-wrapper--empty": !hasChat }}>
       <div class="session-actions-row">
-        <Tooltip value="Start a fresh conversation while keeping the current session intact." placement="top">
-          <Button variant="secondary" size="small" onClick={startSession} aria-label="New Session">
+        <Tooltip
+          value={
+            hasChat
+              ? "Start a fresh conversation while keeping the current session intact."
+              : "This session is already new. Start chatting or create a worktree instead."
+          }
+          placement="top"
+        >
+          <Button
+            variant="secondary"
+            size="small"
+            class="session-new-button"
+            onClick={startSession}
+            disabled={!hasChat}
+            aria-label="New Session"
+          >
             New Session
           </Button>
         </Tooltip>
         <Show when={isSidebar() && server.gitInstalled()}>
-          <div class="session-worktree-split">
+          <div class="session-worktree-split" ref={worktreeRef}>
             <Tooltip value={worktreeTooltip} placement="top">
               <Button
                 variant="secondary"
@@ -187,7 +218,7 @@ export const ChatView: Component<ChatViewProps> = (props) => {
                 New Worktree
               </Button>
             </Tooltip>
-            <DropdownMenu gutter={4} placement="top-end">
+            <DropdownMenu gutter={4} placement="top-start" getAnchorRect={() => worktreeRef?.getBoundingClientRect()}>
               <Tooltip value={advancedTooltip} placement="top">
                 <DropdownMenu.Trigger class="session-worktree-split-arrow" aria-label="Advanced worktree options">
                   <Icon name="chevron-down" size="small" />
@@ -207,7 +238,9 @@ export const ChatView: Component<ChatViewProps> = (props) => {
                   </DropdownMenu.Item>
                   <DropdownMenu.Item onSelect={showAdvancedWorktree}>
                     <Icon name="settings-gear" size="small" />
-                    <DropdownMenu.ItemLabel>Configure New Worktree...</DropdownMenu.ItemLabel>
+                    <DropdownMenu.ItemLabel>
+                      {language.t("agentManager.dialog.configureWorktree")}
+                    </DropdownMenu.ItemLabel>
                   </DropdownMenu.Item>
                 </DropdownMenu.Content>
               </DropdownMenu.Portal>
@@ -216,42 +249,42 @@ export const ChatView: Component<ChatViewProps> = (props) => {
         </Show>
         <Show when={!hasChat}></Show>
         <Show when={hasChat && canContinueInWorktree() && server.gitInstalled()}>
-          <Tooltip
-            value={
-              session.worktreeStats()?.files
-                ? `Move this conversation and ${session.worktreeStats()!.files} changed file${session.worktreeStats()!.files > 1 ? "s" : ""} into a dedicated worktree for isolated follow-up work.`
-                : "Move this conversation and your current local changes into a dedicated worktree for isolated follow-up work."
-            }
-            placement="top"
-          >
-            <Button
-              variant="ghost"
-              size="small"
-              class="session-move-button"
-              classList={{
-                "session-move-button--empty": !session.worktreeStats()?.files,
-                "session-move-button--has-changes": !!session.worktreeStats()?.files,
-              }}
-              disabled={transferring()}
-              onClick={moveToWorktree}
-              aria-label="Move to Worktree"
-            >
-              <Show when={transferring()} fallback={<Icon name="branch" size="small" />}>
-                <Spinner class="chat-spinner-small" />
-              </Show>
-              <span class="session-move-label">{transferring() ? transferDetail() : "Move to Worktree"}</span>
-              <Show when={!transferring() && session.worktreeStats()?.files}>
-                <span class="session-move-tail" aria-hidden="true">
-                  <span class="session-move-divider" />
-                  <span class="session-move-stats">
-                    <Icon name="layers" size="small" />
-                    <span class="session-diff-add">+{session.worktreeStats()!.additions}</span>
-                    <span class="session-diff-del">-{session.worktreeStats()!.deletions}</span>
-                  </span>
-                </span>
-              </Show>
-            </Button>
-          </Tooltip>
+          <div class="session-move-group">
+            <Tooltip value={moveTooltip()} placement="top">
+              <Button
+                variant="ghost"
+                size="small"
+                class="session-move-action"
+                aria-disabled={transferring()}
+                onClick={moveToWorktree}
+                aria-label="Move to Worktree"
+              >
+                <Show when={transferring()} fallback={<Icon name="branch" size="small" />}>
+                  <Spinner class="chat-spinner-small" />
+                </Show>
+                <span class="session-move-label">{transferring() ? transferDetail() : "Move to Worktree"}</span>
+              </Button>
+            </Tooltip>
+            <Tooltip value={changesTooltip()} placement="top">
+              <Button
+                variant="ghost"
+                size="small"
+                class="session-move-changes"
+                classList={{
+                  "session-move-changes--empty": !session.worktreeStats()?.files,
+                  "session-move-changes--has-changes": !!session.worktreeStats()?.files,
+                }}
+                onClick={openChanges}
+                aria-label={language.t("command.session.show.changes")}
+              >
+                <Icon name="layers" size="small" />
+                <Show when={session.worktreeStats()?.files}>
+                  <span class="session-diff-add">+{session.worktreeStats()!.additions}</span>
+                  <span class="session-diff-del">-{session.worktreeStats()!.deletions}</span>
+                </Show>
+              </Button>
+            </Tooltip>
+          </div>
         </Show>
         <div class="session-agent-manager-slot">
           <Tooltip
diff --git a/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx b/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx
index fa1569c469..8912964b30 100644
--- a/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx
+++ b/packages/kilo-vscode/webview-ui/src/components/chat/PromptInput.tsx
@@ -945,7 +945,7 @@ export const PromptInput: Component<PromptInputProps> = (props) => {
                   variant="ghost"
                   size="small"
                   onClick={() => void handleSend()}
-                  disabled={!canSend()}
+                  aria-disabled={!canSend()}
                   aria-label={language.t("prompt.action.send")}
                 >
                   <svg width="16" height="16" viewBox="0 0 16 16" fill="currentColor">
diff --git a/packages/kilo-vscode/webview-ui/src/styles/session-actions.css b/packages/kilo-vscode/webview-ui/src/styles/session-actions.css
index a816c6914e..901b8c04fa 100644
--- a/packages/kilo-vscode/webview-ui/src/styles/session-actions.css
+++ b/packages/kilo-vscode/webview-ui/src/styles/session-actions.css
@@ -63,6 +63,10 @@
   color: var(--vscode-foreground);
 }
 
+.session-actions-row > [data-component="tooltip-trigger"] > [data-component="button"].session-new-button:disabled {
+  cursor: default;
+}
+
 .session-worktree-split {
   display: flex;
   flex: 0 0 auto;
@@ -177,22 +181,57 @@
   font-weight: 600;
 }
 
-/* Diff wrapper also stretches evenly (same flex as buttons) */
-.session-move-button {
+.session-move-group {
+  display: flex;
+  flex: 0 0 auto;
+  align-items: center;
+  gap: 2px;
+  border-radius: var(--session-action-radius);
+  color: var(--vscode-descriptionForeground);
+  transition:
+    background-color 150ms ease,
+    color 150ms ease;
+}
+
+.session-move-group > [data-component="tooltip-trigger"] {
+  display: flex;
+  flex: 0 0 auto;
+}
+
+.session-move-group:hover,
+.session-move-group:has(.session-move-action:focus-visible),
+.session-move-group:has(.session-move-changes:focus-visible) {
+  color: var(--vscode-foreground);
+}
+
+.session-move-group:hover .session-move-action,
+.session-move-group:hover .session-move-changes,
+.session-move-group:has(.session-move-action:focus-visible) .session-move-action,
+.session-move-group:has(.session-move-action:focus-visible) .session-move-changes,
+.session-move-group:has(.session-move-changes:focus-visible) .session-move-action,
+.session-move-group:has(.session-move-changes:focus-visible) .session-move-changes {
+  background: var(--surface-base-hover);
+}
+
+.session-move-action {
   display: flex;
   flex: 0 0 auto;
   align-items: center;
   justify-content: center;
   gap: 5px;
-  border-radius: var(--session-action-radius);
-  color: var(--vscode-descriptionForeground);
+  border-radius: var(--session-action-radius) 0 0 var(--session-action-radius);
+  color: inherit;
   padding: 4px 6px !important;
+  background: transparent;
+  box-shadow: none;
 }
 
-.session-move-button:hover:not(:disabled),
-.session-move-button:focus-visible:not(:disabled),
-.session-move-button:active:not(:disabled) {
-  color: var(--vscode-foreground);
+.session-move-action:hover:not(:disabled),
+.session-move-action:focus-visible:not(:disabled),
+.session-move-action:active:not(:disabled) {
+  color: inherit;
+  background: inherit;
+  box-shadow: none;
 }
 
 .session-move-label {
@@ -202,31 +241,41 @@
   white-space: nowrap;
 }
 
-.session-move-tail {
-  display: inline-flex;
-  align-items: center;
-  gap: 5px;
-  flex-shrink: 0;
-  padding-left: 5px;
-}
-
-.session-move-divider {
-  width: 1px;
-  height: 14px;
-  background: color-mix(in srgb, currentColor 25%, transparent);
+.session-move-action [data-component="icon"],
+.session-move-changes [data-component="icon"] {
   opacity: 0.7;
 }
 
-.session-move-stats {
+.session-move-changes {
   display: inline-flex;
   align-items: center;
   gap: 3px;
-  flex-shrink: 0;
+  flex: 0 0 auto;
+  border-radius: 0 var(--session-action-radius) var(--session-action-radius) 0;
+  color: inherit;
+  padding: 4px 6px !important;
+  background: transparent;
+  box-shadow: none;
+}
+
+.session-move-changes:hover:not(:disabled),
+.session-move-changes:focus-visible:not(:disabled),
+.session-move-changes:active:not(:disabled) {
+  color: inherit;
+  background: inherit;
+  box-shadow: none;
+}
+
+.session-move-changes {
   font-family: var(--font-family-sans);
   font-size: 12px;
   font-variant-numeric: tabular-nums;
 }
 
+.session-move-changes--empty {
+  opacity: 0.7;
+}
+
 .session-agent-manager-slot {
   flex: 0 0 auto;
   margin-left: auto;
@@ -254,10 +303,6 @@
   color: var(--vscode-foreground);
 }
 
-.session-move-stats [data-component="icon"] {
-  opacity: 0.7;
-}
-
 /* Diff stats badge styles retained for the inline move button stats */
 .session-diff-badge {
   display: flex;
@@ -315,21 +360,16 @@
     margin-left: 0;
   }
 
-  .session-move-divider,
   .session-diff-add,
   .session-diff-del {
     display: none;
   }
 
-  .session-move-tail {
-    padding-left: 4px;
-  }
-
-  .session-move-stats {
+  .session-move-changes {
     position: relative;
   }
 
-  .session-move-button--has-changes .session-move-stats [data-component="icon"]::after {
+  .session-move-changes--has-changes [data-component="icon"]::after {
     content: "";
     position: absolute;
     top: -2px;