diff --git a/core/template_filters.py b/core/template_filters.py
new file mode 100644
index 0000000..85a879b
--- /dev/null
+++ b/core/template_filters.py
@@ -0,0 +1,49 @@
+"""Jinja2 custom template filters."""
+
+import re
+from markupsafe import Markup, escape
+
+# Match http(s):// URLs and bare www. URLs
+_URL_RE = re.compile(
+    r'(https?://[^\s<>\"\'\]]+|www\.[^\s<>\"\'\]]+)',
+    re.IGNORECASE,
+)
+
+# Trailing punctuation that usually isn't part of the URL
+_TRAILING_PUNCT = re.compile(r'[.,;:!?\)]+$')
+
+
+def autolink(text):
+    """Detect URLs in plain text and wrap them in clickable <a> tags.
+
+    Escapes all content first (XSS-safe), then replaces URL patterns.
+    Returns Markup so Jinja2 won't double-escape.
+    """
+    if not text:
+        return text
+
+    escaped = str(escape(text))
+
+    def _replace(match):
+        raw = match.group(0)
+        # Strip trailing punctuation that got captured
+        trail = ''
+        m = _TRAILING_PUNCT.search(raw)
+        if m:
+            trail = m.group(0)
+            raw = raw[:m.start()]
+
+        href = raw
+        if raw.lower().startswith('www.'):
+            href = 'https://' + raw
+
+        # Truncate display text for readability
+        display = raw if len(raw) <= 60 else raw[:57] + '...'
+
+        return (
+            f'<a href="{href}" target="_blank" rel="noopener noreferrer" '
+            f'class="autolink">{display}</a>{trail}'
+        )
+
+    result = _URL_RE.sub(_replace, escaped)
+    return Markup(result)
diff --git a/routers/focus.py b/routers/focus.py
index 75c9457..867970d 100644
--- a/routers/focus.py
+++ b/routers/focus.py
@@ -11,9 +11,11 @@ from datetime import date, datetime, timezone
 from core.database import get_db
 from core.base_repository import BaseRepository
 from core.sidebar import get_sidebar_data
+from core.template_filters import autolink
 
 router = APIRouter(prefix="/focus", tags=["focus"])
 templates = Jinja2Templates(directory="templates")
+templates.env.filters["autolink"] = autolink
 
 
 @router.get("/")
diff --git a/routers/lists.py b/routers/lists.py
index 7fdb8f4..8be02a0 100644
--- a/routers/lists.py
+++ b/routers/lists.py
@@ -11,9 +11,11 @@ from datetime import datetime, timezone
 from core.database import get_db
 from core.base_repository import BaseRepository
 from core.sidebar import get_sidebar_data
+from core.template_filters import autolink
 
 router = APIRouter(prefix="/lists", tags=["lists"])
 templates = Jinja2Templates(directory="templates")
+templates.env.filters["autolink"] = autolink
 
 
 @router.get("/")
@@ -187,11 +189,19 @@ async def list_detail(list_id: str, request: Request, db: AsyncSession = Depends
     """))
     all_contacts = [dict(r._mapping) for r in result]
 
+    # All links for insert-into-content picker
+    result = await db.execute(text("""
+        SELECT id, label, url FROM links
+        WHERE is_deleted = false ORDER BY label
+    """))
+    all_links = [dict(r._mapping) for r in result]
+
     return templates.TemplateResponse("list_detail.html", {
         "request": request, "sidebar": sidebar, "item": item,
         "domain": domain, "project": project,
         "list_items": top_items, "child_map": child_map,
         "contacts": contacts, "all_contacts": all_contacts,
+        "all_links": all_links,
         "page_title": item["name"], "active_nav": "lists",
     })
 
diff --git a/static/style.css b/static/style.css
index b30a62e..6eae41a 100644
--- a/static/style.css
+++ b/static/style.css
@@ -1144,6 +1144,53 @@ a:hover { color: var(--accent-hover); }
 }
 .grip-btn:hover { color: var(--accent); }
 
+/* ---- Link Picker & Inline Edit ---- */
+.link-picker {
+    padding: 4px 8px;
+    font-size: 0.8rem;
+    background: var(--surface2);
+    color: var(--muted);
+    border: 1px solid var(--border);
+    border-radius: var(--radius);
+    cursor: pointer;
+}
+.link-picker:hover { border-color: var(--accent); color: var(--text); }
+
+.inline-edit-form {
+    flex: 1;
+    display: flex;
+    align-items: center;
+    gap: 6px;
+    min-width: 0;
+}
+.inline-edit-form input[type="text"] {
+    flex: 1;
+    min-width: 0;
+    padding: 4px 8px;
+    font-size: 0.85rem;
+    background: var(--surface2);
+    color: var(--text);
+    border: 1px solid var(--border);
+    border-radius: var(--radius);
+}
+.inline-edit-form input[type="text"]:focus {
+    border-color: var(--accent);
+    outline: none;
+}
+
+/* ---- Autolinked URLs in list items ---- */
+.autolink {
+    color: var(--accent);
+    text-decoration: underline;
+    text-decoration-color: var(--accent-soft);
+    text-underline-offset: 2px;
+    transition: text-decoration-color var(--transition);
+}
+.autolink:hover {
+    text-decoration-color: var(--accent);
+    color: var(--accent);
+}
+
 /* ---- Scrollbar ---- */
 ::-webkit-scrollbar { width: 6px; }
 ::-webkit-scrollbar-track { background: transparent; }
diff --git a/templates/focus.html b/templates/focus.html
index bc843da..68e798f 100644
--- a/templates/focus.html
+++ b/templates/focus.html
@@ -139,7 +139,7 @@
         {% for li in available_list_items %}
         <div class="list-row{% if loop.index > 25 %} focus-hidden-item hidden{% endif %}" style="padding:3px 8px;min-height:0;">
             <span style="color:var(--muted);font-size:0.85rem;margin-right:4px">&#9776;</span>
-            <span class="row-title">{{ li.content }}</span>
+            <span class="row-title">{{ li.content|autolink }}</span>
             {% if li.list_name %}<span class="row-tag" style="background:var(--purple);color:#fff">{{ li.list_name }}</span>{% endif %}
             <form action="/focus/add" method="post" style="display:inline">
                 <input type="hidden" name="list_item_id" value="{{ li.id }}">
diff --git a/templates/list_detail.html b/templates/list_detail.html
index 94986f3..ab34539 100644
--- a/templates/list_detail.html
+++ b/templates/list_detail.html
@@ -37,7 +37,15 @@
 
 <!-- Add item form -->
 <form class="quick-add mt-3" action="/lists/{{ item.id }}/items/add" method="post">
-    <input type="text" name="content" placeholder="Add item..." required>
+    <input type="text" name="content" id="add-item-content" placeholder="Add item..." required style="flex:1">
+    {% if all_links %}
+    <select class="link-picker" data-target="add-item-content" style="max-width:180px">
+        <option value="">Insert link...</option>
+        {% for lnk in all_links %}
+        <option value="{{ lnk.url }}">{{ lnk.label }}</option>
+        {% endfor %}
+    </select>
+    {% endif %}
     <button type="submit" class="btn btn-primary btn-sm">Add</button>
 </form>
 
@@ -58,14 +66,29 @@
             </form>
         </div>
         {% endif %}
-        <span class="row-title" style="{{ 'text-decoration: line-through; opacity: 0.6;' if li.completed }}">
-            {{ li.content }}
+        <span class="row-title" data-display-for="{{ li.id }}" style="{{ 'text-decoration: line-through; opacity: 0.6;' if li.completed }}">
+            {{ li.content|autolink }}
         </span>
-        <div class="row-actions">
+        <div class="row-actions" data-display-for="{{ li.id }}">
+            <button type="button" class="btn btn-ghost btn-xs edit-item-btn" data-item-id="{{ li.id }}">Edit</button>
             <form action="/lists/{{ item.id }}/items/{{ li.id }}/delete" method="post" style="display:inline">
                 <button type="submit" class="btn btn-ghost btn-xs" style="color: var(--red)">Del</button>
             </form>
         </div>
+        <!-- Inline edit form -->
+        <form class="inline-edit-form" data-edit-for="{{ li.id }}" action="/lists/{{ item.id }}/items/{{ li.id }}/edit" method="post" style="display:none;">
+            <input type="text" name="content" id="edit-content-{{ li.id }}" value="{{ li.content }}" required style="flex:1">
+            {% if all_links %}
+            <select class="link-picker" data-target="edit-content-{{ li.id }}" style="max-width:160px">
+                <option value="">Insert link...</option>
+                {% for lnk in all_links %}
+                <option value="{{ lnk.url }}">{{ lnk.label }}</option>
+                {% endfor %}
+            </select>
+            {% endif %}
+            <button type="submit" class="btn btn-primary btn-xs">Save</button>
+            <button type="button" class="btn btn-ghost btn-xs cancel-edit-btn" data-item-id="{{ li.id }}">Cancel</button>
+        </form>
     </div>
 
     <!-- Child items -->
@@ -83,14 +106,29 @@
             </form>
         </div>
         {% endif %}
-        <span class="row-title" style="{{ 'text-decoration: line-through; opacity: 0.6;' if child.completed }}">
-            {{ child.content }}
+        <span class="row-title" data-display-for="{{ child.id }}" style="{{ 'text-decoration: line-through; opacity: 0.6;' if child.completed }}">
+            {{ child.content|autolink }}
         </span>
-        <div class="row-actions">
+        <div class="row-actions" data-display-for="{{ child.id }}">
+            <button type="button" class="btn btn-ghost btn-xs edit-item-btn" data-item-id="{{ child.id }}">Edit</button>
             <form action="/lists/{{ item.id }}/items/{{ child.id }}/delete" method="post" style="display:inline">
                 <button type="submit" class="btn btn-ghost btn-xs" style="color: var(--red)">Del</button>
             </form>
         </div>
+        <!-- Inline edit form -->
+        <form class="inline-edit-form" data-edit-for="{{ child.id }}" action="/lists/{{ item.id }}/items/{{ child.id }}/edit" method="post" style="display:none;">
+            <input type="text" name="content" id="edit-content-{{ child.id }}" value="{{ child.content }}" required style="flex:1">
+            {% if all_links %}
+            <select class="link-picker" data-target="edit-content-{{ child.id }}" style="max-width:160px">
+                <option value="">Insert link...</option>
+                {% for lnk in all_links %}
+                <option value="{{ lnk.url }}">{{ lnk.label }}</option>
+                {% endfor %}
+            </select>
+            {% endif %}
+            <button type="submit" class="btn btn-primary btn-xs">Save</button>
+            <button type="button" class="btn btn-ghost btn-xs cancel-edit-btn" data-item-id="{{ child.id }}">Cancel</button>
+        </form>
     </div>
     {% endfor %}
     {% endfor %}
@@ -135,4 +173,49 @@
     <div style="padding: 12px; color: var(--muted); font-size: 0.85rem;">No contacts linked</div>
     {% endfor %}
 </div>
+<script>
+(function() {
+    // Link picker: insert URL at cursor position in target input
+    document.querySelectorAll('.link-picker').forEach(function(sel) {
+        sel.addEventListener('change', function() {
+            var url = sel.value;
+            if (!url) return;
+            var targetId = sel.getAttribute('data-target');
+            var input = document.getElementById(targetId);
+            if (!input) return;
+            var start = input.selectionStart || input.value.length;
+            var end = input.selectionEnd || input.value.length;
+            var before = input.value.substring(0, start);
+            var after = input.value.substring(end);
+            // Add space padding if needed
+            if (before.length > 0 && before[before.length - 1] !== ' ') before += ' ';
+            if (after.length > 0 && after[0] !== ' ') url += ' ';
+            input.value = before + url + after;
+            input.focus();
+            var pos = before.length + url.length;
+            input.setSelectionRange(pos, pos);
+            sel.selectedIndex = 0;
+        });
+    });
+
+    // Inline edit: toggle edit form
+    document.querySelectorAll('.edit-item-btn').forEach(function(btn) {
+        btn.addEventListener('click', function() {
+            var id = btn.getAttribute('data-item-id');
+            document.querySelectorAll('[data-display-for="' + id + '"]').forEach(function(el) { el.style.display = 'none'; });
+            var form = document.querySelector('[data-edit-for="' + id + '"]');
+            if (form) { form.style.display = 'flex'; form.querySelector('input[name="content"]').focus(); }
+        });
+    });
+
+    document.querySelectorAll('.cancel-edit-btn').forEach(function(btn) {
+        btn.addEventListener('click', function() {
+            var id = btn.getAttribute('data-item-id');
+            document.querySelectorAll('[data-display-for="' + id + '"]').forEach(function(el) { el.style.display = ''; });
+            var form = document.querySelector('[data-edit-for="' + id + '"]');
+            if (form) form.style.display = 'none';
+        });
+    });
+})();
+</script>
 {% endblock %}