diff --git a/static/index.html b/static/index.html
index 7709ad28a..ca939297d 100644
--- a/static/index.html
+++ b/static/index.html
@@ -242,7 +242,7 @@
   </script>
   <!-- Memory Management Modal -->
   <div id="memory-modal" class="modal hidden">
-    <div class="modal-content memory-modal-content" style="background:var(--bg)">
+    <div class="modal-content memory-modal-content" role="dialog" aria-label="Brain" style="background:var(--bg)">
       <div class="modal-header">
         <h4><svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" style="vertical-align:-2px;margin-right:6px"><path d="M12 5a3 3 0 1 0-5.997.125 4 4 0 0 0-2.526 5.77 4 4 0 0 0 .556 6.588A4 4 0 1 0 12 18Z"/><path d="M12 5a3 3 0 1 1 5.997.125 4 4 0 0 1 2.526 5.77 4 4 0 0 1-.556 6.588A4 4 0 1 1 12 18Z"/><path d="M15 13a4.5 4.5 0 0 1-3-4 4.5 4.5 0 0 1-3 4"/></svg>Brain</h4>
         <button class="close-btn" id="close-memory-modal" aria-label="Close memory modal">✖</button>
@@ -432,14 +432,14 @@
 
   <!-- Theme Popup (floating panel) -->
   <div id="theme-modal" class="modal hidden">
-  <div id="theme-popup" class="modal-content admin-modal-content" style="background:var(--bg)">
+  <div id="theme-popup" class="modal-content admin-modal-content" role="dialog" aria-label="Theme" style="background:var(--bg)">
     <div class="modal-header theme-popup-header" id="theme-popup-header">
       <h4><svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" style="vertical-align:-2px;margin-right:6px"><circle cx="12" cy="12" r="10"/><path d="M12 2a7 7 0 0 0 0 20 4 4 0 0 1 0-8 4 4 0 0 0 0-8"/><circle cx="8" cy="9" r="1.5" fill="currentColor"/><circle cx="15" cy="14" r="1.5" fill="currentColor"/><circle cx="9" cy="15" r="1.5" fill="currentColor"/></svg>Theme</h4>
       <button type="button" class="theme-opacity-wrap theme-opacity-toggle hidden" id="theme-opacity-wrap" title="Fade this window to preview the page behind it" aria-pressed="false">
         <svg width="11" height="11" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" aria-hidden="true"><path d="M1 12s4-8 11-8 11 8 11 8-4 8-11 8-11-8-11-8z"/><circle cx="12" cy="12" r="3"/></svg>
         <span class="theme-opacity-label">Peek</span>
       </button>
-      <button class="close-btn" id="close-theme-popup">&#x2716;</button>
+      <button class="close-btn" id="close-theme-popup" aria-label="Close theme">&#x2716;</button>
     </div>
     <!-- Theme tabs -->
     <div class="admin-tabs" id="theme-tabs">
@@ -1115,10 +1115,10 @@
 
     <!-- Character (custom preset) modal -->
     <div id="custom-preset-modal" class="modal hidden">
-      <div class="modal-content preset-modal-content" style="background:var(--bg)">
+      <div class="modal-content preset-modal-content" role="dialog" aria-label="Prompt" style="background:var(--bg)">
         <div class="modal-header">
           <h4><svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" style="vertical-align:-2px;margin-right:6px"><path d="m18 2 4 4"/><path d="m17 7 3-3"/><path d="M19 9 8.7 19.3c-1 1-2.5 1-3.4 0l-.6-.6c-1-1-1-2.5 0-3.4L15 5"/><path d="m9 11 4 4"/><path d="m5 19-3 3"/><path d="m14 4 6 6"/></svg>Prompt</h4>
-          <button class="close-btn" id="close-custom-preset">✖</button>
+          <button class="close-btn" id="close-custom-preset" aria-label="Close prompt">✖</button>
         </div>
         <div class="modal-body preset-modal-body">
           <div id="char-fields-wrap">
@@ -1262,7 +1262,7 @@
 
   <!-- Rename Session Modal -->
   <div id="rename-session-modal" class="modal hidden">
-    <div class="modal-content" style="width: 400px;">
+    <div class="modal-content" role="dialog" aria-label="Rename session" style="width: 400px;">
       <div class="modal-header">
         <h4>Rename Session</h4>
         <button class="close-btn" id="close-rename-session" aria-label="Close rename session modal">✖</button>
@@ -1288,10 +1288,10 @@
 
   <!-- Cookbook Modal -->
   <div id="cookbook-modal" class="modal hidden">
-    <div class="modal-content" style="width: min(780px, 92vw); height: 94vh; max-height: 94vh; background: var(--bg);">
+    <div class="modal-content" role="dialog" aria-label="Cookbook" style="width: min(780px, 92vw); height: 94vh; max-height: 94vh; background: var(--bg);">
       <div class="modal-header">
         <h4 style="margin:0;margin-right:auto"><svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" style="vertical-align:-2px;margin-right:6px"><path d="M12 7v14"/><path d="M3 18a1 1 0 0 1-1-1V4a1 1 0 0 1 1-1h5a4 4 0 0 1 4 4 4 4 0 0 1 4-4h5a1 1 0 0 1 1 1v13a1 1 0 0 1-1 1h-6a3 3 0 0 0-3 3 3 3 0 0 0-3-3z"/></svg>Cookbook</h4>
-        <button class="close-btn" id="close-cookbook-modal">✖</button>
+        <button class="close-btn" id="close-cookbook-modal" aria-label="Close cookbook">✖</button>
       </div>
       <div class="modal-body cookbook-body"></div>
     </div>
@@ -1299,14 +1299,14 @@
 
   <!-- Settings Modal (all users) -->
   <div id="settings-modal" class="modal hidden">
-    <div class="modal-content settings-modal-content">
+    <div class="modal-content settings-modal-content" role="dialog" aria-label="Settings">
       <div class="modal-header">
         <h4><span style="vertical-align:-1px;margin-right:6px;font-size:15px">&#x2699;</span>Settings</h4>
         <button type="button" class="theme-opacity-wrap theme-opacity-toggle hidden" id="settings-opacity-wrap" title="Fade this window to preview the page behind it" aria-pressed="false">
           <svg width="11" height="11" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" aria-hidden="true"><path d="M1 12s4-8 11-8 11 8 11 8-4 8-11 8-11-8-11-8z"></path><circle cx="12" cy="12" r="3"></circle></svg>
           <span class="theme-opacity-label">Peek</span>
         </button>
-        <button class="close-btn">✖</button>
+        <button class="close-btn" aria-label="Close settings">✖</button>
       </div>
       <div class="admin-toggle-sub" style="padding:0 12px 8px;opacity:0.6;font-size:11px;">Toggle on/off visibility of tools and modules across the interface.</div>
       <div class="settings-layout">
diff --git a/static/js/ui.js b/static/js/ui.js
index f535578fa..aa82cc616 100644
--- a/static/js/ui.js
+++ b/static/js/ui.js
@@ -579,8 +579,8 @@ export function styledConfirm(message, { confirmText = 'Confirm', cancelText = '
       overlay.id = 'styled-confirm-overlay';
       overlay.className = 'modal';
       overlay.innerHTML =
-        '<div class="modal-content styled-confirm-box">' +
-          '<div class="modal-header"><h4>Confirm</h4></div>' +
+        '<div class="modal-content styled-confirm-box" role="dialog" aria-modal="true" aria-labelledby="styled-confirm-title" aria-describedby="styled-confirm-msg">' +
+          '<div class="modal-header"><h4 id="styled-confirm-title">Confirm</h4></div>' +
           '<div class="modal-body"><p id="styled-confirm-msg"></p></div>' +
           '<div class="modal-footer">' +
             '<button id="styled-confirm-cancel"></button>' +
@@ -600,6 +600,8 @@ export function styledConfirm(message, { confirmText = 'Confirm', cancelText = '
     okBtn.className = danger ? 'confirm-btn confirm-btn-danger' : 'confirm-btn confirm-btn-primary';
     cancelBtn.className = 'confirm-btn confirm-btn-secondary';
 
+    // Remember what had focus so we can restore it when the dialog closes.
+    const _prevFocus = document.activeElement;
     overlay.classList.remove('hidden');
     overlay.style.display = '';
 
@@ -610,6 +612,7 @@ export function styledConfirm(message, { confirmText = 'Confirm', cancelText = '
       cancelBtn.removeEventListener('click', onCancel);
       overlay.removeEventListener('click', onBackdrop);
       document.removeEventListener('keydown', onKey);
+      try { _prevFocus && _prevFocus.focus && _prevFocus.focus(); } catch {}
       resolve(result);
     }
     function onOk() { cleanup(true); }
@@ -626,6 +629,13 @@ export function styledConfirm(message, { confirmText = 'Confirm', cancelText = '
         e.stopPropagation();
         e.stopImmediatePropagation();
         cleanup(false);
+      } else if (e.key === 'Tab') {
+        // Trap focus inside the dialog so Tab can't wander to the page behind.
+        e.preventDefault();
+        const f = [cancelBtn, okBtn];
+        const i = f.indexOf(document.activeElement);
+        const n = e.shiftKey ? (i <= 0 ? f.length - 1 : i - 1) : (i >= f.length - 1 ? 0 : i + 1);
+        f[n].focus();
       }
     }
 
@@ -656,7 +666,7 @@ export function styledPrompt(message, {
       overlay.id = 'styled-prompt-overlay';
       overlay.className = 'modal';
       overlay.innerHTML =
-        '<div class="modal-content styled-confirm-box styled-prompt-box">' +
+        '<div class="modal-content styled-confirm-box styled-prompt-box" role="dialog" aria-modal="true" aria-labelledby="styled-prompt-title" aria-describedby="styled-prompt-msg">' +
           '<div class="modal-header"><h4 id="styled-prompt-title"></h4></div>' +
           '<div class="modal-body">' +
             '<p id="styled-prompt-msg"></p>' +
@@ -685,6 +695,8 @@ export function styledPrompt(message, {
     okBtn.textContent = confirmText;
     cancelBtn.textContent = cancelText;
 
+    // Remember what had focus so we can restore it when the dialog closes.
+    const _prevFocus = document.activeElement;
     overlay.classList.remove('hidden');
     overlay.style.display = '';
 
@@ -696,6 +708,7 @@ export function styledPrompt(message, {
       overlay.removeEventListener('click', onBackdrop);
       document.removeEventListener('keydown', onKey);
       input.removeEventListener('keydown', onInputKey);
+      try { _prevFocus && _prevFocus.focus && _prevFocus.focus(); } catch {}
       resolve(result);
     }
     function onOk() { cleanup((input.value || '').trim()); }
@@ -707,6 +720,13 @@ export function styledPrompt(message, {
         e.stopPropagation();
         e.stopImmediatePropagation();
         cleanup(null);
+      } else if (e.key === 'Tab') {
+        // Trap focus inside the dialog (input → Cancel → OK → input …).
+        e.preventDefault();
+        const f = [input, cancelBtn, okBtn];
+        const i = f.indexOf(document.activeElement);
+        const n = e.shiftKey ? (i <= 0 ? f.length - 1 : i - 1) : (i >= f.length - 1 ? 0 : i + 1);
+        f[n].focus();
       }
     }
     function onInputKey(e) {
diff --git a/tests/test_dialog_aria.py b/tests/test_dialog_aria.py
new file mode 100644
index 000000000..be6cb3392
--- /dev/null
+++ b/tests/test_dialog_aria.py
@@ -0,0 +1,56 @@
+"""Pin the dialog accessibility semantics added for the roadmap a11y pass.
+
+Screen readers only announce "dialog" (and its name) when the container
+carries role="dialog" plus an accessible name. These checks lock that in for
+the static modals in index.html and the JS-built confirm/prompt dialogs, and
+guard against a close button shipping without an accessible label again.
+
+Plain text/regex assertions (no bs4 dependency), matching the lightweight style
+of the other tests in this suite.
+"""
+import re
+from pathlib import Path
+
+_REPO = Path(__file__).resolve().parent.parent
+_INDEX = (_REPO / "static" / "index.html").read_text(encoding="utf-8")
+_UI = (_REPO / "static" / "js" / "ui.js").read_text(encoding="utf-8")
+
+
+def test_static_modals_expose_dialog_role_and_name():
+    # Each static tool window must announce itself as a named dialog. These are
+    # dockable/tiling windows, so they are role="dialog" WITHOUT aria-modal.
+    for name in ("Brain", "Theme", "Prompt", "Rename session", "Cookbook", "Settings"):
+        assert f'role="dialog" aria-label="{name}"' in _INDEX, f"missing dialog role/name for {name!r}"
+
+
+def test_no_modal_close_button_is_unlabeled():
+    # Every .close-btn must carry an accessible name (text glyph alone reads as
+    # "heavy multiplication x"). Catch any new close button that forgets one.
+    buttons = re.findall(r'<button[^>]*class="close-btn"[^>]*>', _INDEX)
+    assert buttons, "expected to find close-btn buttons in index.html"
+    unlabeled = [b for b in buttons if "aria-label=" not in b]
+    assert not unlabeled, f"close buttons missing aria-label: {unlabeled}"
+
+
+def test_styled_confirm_and_prompt_are_modal_dialogs():
+    # The JS-built confirm/prompt overlays ARE blocking modals, so they get
+    # role="dialog" + aria-modal="true" and are labelled by their title.
+    assert 'class="modal-content styled-confirm-box" role="dialog" aria-modal="true"' in _UI
+    assert 'aria-labelledby="styled-confirm-title"' in _UI
+    assert '<h4 id="styled-confirm-title">Confirm</h4>' in _UI
+
+    assert 'styled-prompt-box" role="dialog" aria-modal="true"' in _UI
+    assert 'aria-labelledby="styled-prompt-title"' in _UI
+    # The label/description targets the styled-prompt dialog points at must exist.
+    assert 'id="styled-prompt-title"' in _UI
+    assert 'id="styled-prompt-msg"' in _UI
+
+
+def test_styled_dialogs_manage_focus():
+    # A dialog is only really accessible if it restores focus to the trigger on
+    # close and traps Tab while open. Both styledConfirm and styledPrompt should
+    # capture the previously-focused element, restore it, and trap Tab.
+    assert _UI.count("const _prevFocus = document.activeElement;") == 2
+    assert _UI.count("_prevFocus && _prevFocus.focus && _prevFocus.focus()") == 2
+    assert _UI.count("e.key === 'Tab'") == 2
+