diff --git a/frontend/src/components/FloatingTranscriptDebug.vue b/frontend/src/components/FloatingTranscriptDebug.vue
index a2a076a..437ddcf 100644
--- a/frontend/src/components/FloatingTranscriptDebug.vue
+++ b/frontend/src/components/FloatingTranscriptDebug.vue
@@ -72,6 +72,17 @@ const dragOffset = ref({ x: 0, y: 0 })
 const isResizing = ref(false)
 const size = ref({ w: 480, h: 600 })
 
+// Size mode: pin (small, anchored to FAB), medium (default), large
+type SizeMode = 'pin' | 'medium' | 'large'
+const sizeMode = ref<SizeMode>('medium')
+
+function cycleSizeMode() {
+  const modes: SizeMode[] = ['pin', 'medium', 'large']
+  const i = modes.indexOf(sizeMode.value)
+  sizeMode.value = modes[(i + 1) % modes.length]
+  hasCustomPosition.value = false
+}
+
 // Mobile bottom sheet state
 const isMobile = ref(false)
 const sheetHeight = ref(55)
@@ -217,6 +228,12 @@ function stopResize() {
 // COMPUTED STYLE
 // ============================================================================
 
+const sizeModePresets: Record<SizeMode, { w: number; h: number }> = {
+  pin: { w: 240, h: 300 },
+  medium: { w: 480, h: 600 },
+  large: { w: 800, h: 760 }
+}
+
 const windowStyle = computed((): Record<string, string> => {
   if (isMobile.value) {
     return {
@@ -230,21 +247,48 @@ const windowStyle = computed((): Record<string, string> => {
     }
   }
 
-  if (!hasCustomPosition.value) {
+  const preset = sizeModePresets[sizeMode.value]
+
+  // Custom position from dragging (uses current resize size or preset)
+  if (hasCustomPosition.value) {
+    const w = sizeMode.value === 'medium' ? size.value.w : preset.w
+    const h = sizeMode.value === 'medium' ? size.value.h : preset.h
     return {
-      width: `${size.value.w}px`,
-      height: `${size.value.h}px`,
+      width: `${w}px`,
+      height: `${h}px`,
+      top: `${position.value.y}px`,
+      left: `${position.value.x}px`,
+      bottom: 'auto',
+      right: 'auto'
+    }
+  }
+
+  // Pin: anchored to FAB button (bottom-left corner aligned)
+  if (sizeMode.value === 'pin') {
+    return {
+      width: `${preset.w}px`,
+      height: `${preset.h}px`,
+      bottom: '20px',
+      left: '80px'
+    }
+  }
+
+  // Large: centered-ish, generous size
+  if (sizeMode.value === 'large') {
+    return {
+      width: `${preset.w}px`,
+      height: `${preset.h}px`,
       bottom: '16px',
       left: '90px'
     }
   }
+
+  // Medium (default)
   return {
     width: `${size.value.w}px`,
     height: `${size.value.h}px`,
-    top: `${position.value.y}px`,
-    left: `${position.value.x}px`,
-    bottom: 'auto',
-    right: 'auto'
+    bottom: '16px',
+    left: '90px'
   }
 })
 
@@ -352,6 +396,22 @@ onBeforeUnmount(() => {
               <span v-if="selectedAgent" class="agent-badge">{{ selectedAgent }}</span>
             </div>
             <div class="window-controls">
+              <button @click.stop="cycleSizeMode" class="size-btn" :title="`Size: ${sizeMode}`">
+                <!-- Pin icon: small square bottom-left -->
+                <svg v-if="sizeMode === 'pin'" width="10" height="10" viewBox="0 0 10 10" shape-rendering="crispEdges">
+                  <rect x="0" y="6" width="4" height="4" fill="currentColor"/>
+                </svg>
+                <!-- Medium icon: medium square centered -->
+                <svg v-else-if="sizeMode === 'medium'" width="10" height="10" viewBox="0 0 10 10" shape-rendering="crispEdges">
+                  <rect x="2" y="2" width="6" height="6" fill="currentColor" opacity="0.35"/>
+                  <rect x="3" y="3" width="4" height="4" fill="currentColor"/>
+                </svg>
+                <!-- Large icon: full square -->
+                <svg v-else width="10" height="10" viewBox="0 0 10 10" shape-rendering="crispEdges">
+                  <rect x="0" y="0" width="10" height="10" fill="currentColor" opacity="0.35"/>
+                  <rect x="1" y="1" width="8" height="8" fill="currentColor"/>
+                </svg>
+              </button>
               <button @click.stop="showSelector = !showSelector" :class="{ active: showSelector }" title="Agent/Session">
                 <svg width="10" height="10" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2">
                   <circle cx="12" cy="12" r="3"/>
@@ -409,6 +469,7 @@ onBeforeUnmount(() => {
           <!-- Content -->
           <div class="content">
             <BackgroundPixelArt />
+            <div class="readability-overlay" />
             <ChatContainer
               v-if="conversation"
               :conversation="conversation"
@@ -435,9 +496,15 @@ onBeforeUnmount(() => {
 <style scoped>
 .aero-win {
   position: fixed;
-  min-width: 360px;
-  min-height: 300px;
+  min-width: 200px;
+  min-height: 200px;
   z-index: 9999;
+  transition: width 0.3s ease, height 0.3s ease, top 0.3s ease, left 0.3s ease, bottom 0.3s ease;
+}
+
+.aero-win.dragging,
+.aero-win.resizing {
+  transition: none;
 }
 
 .glass {
@@ -507,13 +574,20 @@ onBeforeUnmount(() => {
   pointer-events: none !important;
 }
 
-/* Idle: slide user-input down and fade out */
+/* Idle: slide user-input down and fade out (only if empty) */
 .aero-win:not(.chrome-visible) .content :deep(.user-input) {
   opacity: 0 !important;
   transform: translateY(100%) !important;
   pointer-events: none !important;
 }
 
+/* Keep user-input visible when textarea has text */
+.aero-win:not(.chrome-visible) .content :deep(.user-input:has(.input-field:not(:placeholder-shown))) {
+  opacity: 1 !important;
+  transform: none !important;
+  pointer-events: auto !important;
+}
+
 /* Idle: also hide selection bar */
 .aero-win:not(.chrome-visible) .content :deep(.selection-bar) {
   opacity: 0 !important;
@@ -643,6 +717,16 @@ onBeforeUnmount(() => {
   color: #a5b4fc;
 }
 
+.window-controls .size-btn {
+  color: #0ea5e9;
+}
+
+.window-controls .size-btn:hover {
+  color: #38bdf8;
+  background: rgba(14, 165, 233, 0.15);
+  border-color: rgba(14, 165, 233, 0.25);
+}
+
 .window-controls button.x:hover {
   background: rgba(239, 68, 68, 0.3);
   border-color: rgba(239, 68, 68, 0.4);
@@ -772,6 +856,21 @@ onBeforeUnmount(() => {
   /* Background handled by BackgroundPixelArt component */
 }
 
+/* Dark readability overlay: between ocean bg (z-index:0) and chat (z-index:1) */
+.readability-overlay {
+  position: absolute;
+  inset: 0;
+  z-index: 0;
+  background: rgba(0, 0, 0, 0.55);
+  pointer-events: none;
+  opacity: 0;
+  transition: opacity 0.35s ease;
+}
+
+.aero-win.chrome-visible .readability-overlay {
+  opacity: 1;
+}
+
 /* Override ChatContainer backgrounds: glass-transparent */
 .content :deep(.chat-container) {
   background: transparent !important;