diff --git a/src/renderer/components/Toolbar.tsx b/src/renderer/components/Toolbar.tsx
index 325def8..4f3fc3d 100644
--- a/src/renderer/components/Toolbar.tsx
+++ b/src/renderer/components/Toolbar.tsx
@@ -621,10 +621,11 @@ export default function Toolbar({ onOpenSettings, settingsOpen }: ToolbarProps):
 
         <button
           type="button"
-          className={`toolbar__icon-button ${isAlwaysOnTop ? 'is-active' : ''}`.trim()}
+          className={`toolbar__icon-button toolbar__icon-button--pin ${isAlwaysOnTop ? 'is-active' : ''}`.trim()}
           onClick={handlePin}
           title={isAlwaysOnTop ? 'Unpin from top' : 'Pin to top'}
           aria-label={isAlwaysOnTop ? 'Unpin from top' : 'Pin to top'}
+          aria-pressed={isAlwaysOnTop}
         >
           <PinIcon />
         </button>
diff --git a/src/renderer/popouts/ScopePopoutWindow.tsx b/src/renderer/popouts/ScopePopoutWindow.tsx
index de7f85c..de42051 100644
--- a/src/renderer/popouts/ScopePopoutWindow.tsx
+++ b/src/renderer/popouts/ScopePopoutWindow.tsx
@@ -259,10 +259,11 @@ export default function ScopePopoutWindow({ scopeKind }: ScopePopoutWindowProps)
             <div className="scope-popout__actions">
               <button
                 type="button"
-                className={`scope-popout__button ${isAlwaysOnTop ? 'is-active' : ''}`.trim()}
+                className={`scope-popout__button scope-popout__button--pin ${isAlwaysOnTop ? 'is-active' : ''}`.trim()}
                 onClick={() => window.electronAPI.toggleAlwaysOnTop()}
                 aria-label={isAlwaysOnTop ? 'Unpin from top' : 'Pin to top'}
                 title={isAlwaysOnTop ? 'Unpin from top' : 'Pin to top'}
+                aria-pressed={isAlwaysOnTop}
               >
                 <PinIcon />
               </button>
diff --git a/src/renderer/styles/globals.css b/src/renderer/styles/globals.css
index a5870d6..7627011 100644
--- a/src/renderer/styles/globals.css
+++ b/src/renderer/styles/globals.css
@@ -780,10 +780,26 @@ button.toolbar__version:hover {
   transform: translateY(-1px);
 }
 
-.toolbar__icon-button.is-active {
+.toolbar__icon-button.is-active,
+.toolbar__icon-button.is-active:hover:not(:disabled) {
   color: var(--accent);
   border-color: var(--control-border-active);
   background: var(--control-bg-active);
+  transform: none;
+}
+
+.toolbar__icon-button--pin:hover:not(:disabled):not(.is-active) {
+  border-color: var(--control-border);
+  background: var(--control-bg);
+}
+
+.toolbar__icon-button--pin.is-active,
+.toolbar__icon-button--pin.is-active:hover:not(:disabled) {
+  border-color: var(--accent);
+}
+
+.toolbar__icon-button--pin.is-active svg path {
+  fill: currentColor;
 }
 
 .toolbar__icon-button--danger:hover:not(:disabled) {
@@ -2407,12 +2423,33 @@ button.toolbar__version:hover {
   height: 14px;
 }
 
-.scope-popout__button:hover:not(:disabled),
-.scope-popout__button.is-active {
+.scope-popout__button:hover:not(:disabled) {
+  color: var(--control-text);
+  border-color: var(--control-border-active);
+  background: var(--control-bg-hover);
+  transform: translateY(-1px);
+}
+
+.scope-popout__button.is-active,
+.scope-popout__button.is-active:hover:not(:disabled) {
   color: var(--accent);
   border-color: var(--control-border-active);
   background: var(--control-bg-active);
-  transform: translateY(-1px);
+  transform: none;
+}
+
+.scope-popout__button--pin:hover:not(:disabled):not(.is-active) {
+  border-color: transparent;
+  background: var(--control-bg);
+}
+
+.scope-popout__button--pin.is-active,
+.scope-popout__button--pin.is-active:hover:not(:disabled) {
+  border-color: var(--accent);
+}
+
+.scope-popout__button--pin.is-active svg path {
+  fill: currentColor;
 }
 
 .scope-popout__button:disabled {
diff --git a/test/renderer-helpers.test.ts b/test/renderer-helpers.test.ts
index f4520e8..6a0236d 100644
--- a/test/renderer-helpers.test.ts
+++ b/test/renderer-helpers.test.ts
@@ -3992,6 +3992,40 @@ test('BottomBar close button uses flat themed control backgrounds', async () =>
   assert.doesNotMatch(closeHoverBlock, /linear-gradient/)
 })
 
+test('pin buttons use a persistent filled active state distinct from inactive hover', async () => {
+  const toolbarSource = await readFile(join(process.cwd(), 'src', 'renderer', 'components', 'Toolbar.tsx'), 'utf8')
+  const popoutSource = await readFile(join(process.cwd(), 'src', 'renderer', 'popouts', 'ScopePopoutWindow.tsx'), 'utf8')
+  const stylesSource = await readFile(join(process.cwd(), 'src', 'renderer', 'styles', 'globals.css'), 'utf8')
+  const toolbarHoverBlock = stylesSource.match(
+    /\.toolbar__icon-button--pin:hover:not\(:disabled\):not\(\.is-active\) \{([\s\S]*?)\n\}/,
+  )?.[1]
+  const toolbarActiveBlock = stylesSource.match(
+    /\.toolbar__icon-button--pin\.is-active,\n\.toolbar__icon-button--pin\.is-active:hover:not\(:disabled\) \{([\s\S]*?)\n\}/,
+  )?.[1]
+  const popoutHoverBlock = stylesSource.match(
+    /\.scope-popout__button--pin:hover:not\(:disabled\):not\(\.is-active\) \{([\s\S]*?)\n\}/,
+  )?.[1]
+  const popoutActiveBlock = stylesSource.match(
+    /\.scope-popout__button--pin\.is-active,\n\.scope-popout__button--pin\.is-active:hover:not\(:disabled\) \{([\s\S]*?)\n\}/,
+  )?.[1]
+
+  assert.match(toolbarSource, /toolbar__icon-button toolbar__icon-button--pin/)
+  assert.match(toolbarSource, /aria-pressed=\{isAlwaysOnTop\}/)
+  assert.match(popoutSource, /scope-popout__button scope-popout__button--pin/)
+  assert.match(popoutSource, /aria-pressed=\{isAlwaysOnTop\}/)
+  assert.ok(toolbarHoverBlock)
+  assert.ok(toolbarActiveBlock)
+  assert.ok(popoutHoverBlock)
+  assert.ok(popoutActiveBlock)
+
+  assert.match(toolbarHoverBlock, /background: var\(--control-bg\);/)
+  assert.match(popoutHoverBlock, /background: var\(--control-bg\);/)
+  assert.match(toolbarActiveBlock, /border-color: var\(--accent\);/)
+  assert.match(popoutActiveBlock, /border-color: var\(--accent\);/)
+  assert.match(stylesSource, /\.toolbar__icon-button--pin\.is-active svg path \{\n  fill: currentColor;/)
+  assert.match(stylesSource, /\.scope-popout__button--pin\.is-active svg path \{\n  fill: currentColor;/)
+})
+
 test('toolbar uses the Prism logo support link and static package icons are configured', async () => {
   const toolbarSource = await readFile(join(process.cwd(), 'src', 'renderer', 'components', 'Toolbar.tsx'), 'utf8')
   const stylesSource = await readFile(join(process.cwd(), 'src', 'renderer', 'styles', 'globals.css'), 'utf8')