diff --git a/src/renderer/components/SessionList.tsx b/src/renderer/components/SessionList.tsx
index 6add0987..2194c3bf 100644
--- a/src/renderer/components/SessionList.tsx
+++ b/src/renderer/components/SessionList.tsx
@@ -2640,12 +2640,29 @@ function SessionListInner(props: SessionListProps) {
 
 					{/* SESSIONS - Flat list when no groups exist, otherwise show Ungrouped folder */}
 					{sessions.length > 0 && groups.length === 0 ? (
-						/* FLAT LIST - No groups exist yet, show sessions directly */
-						<div className="flex flex-col">
-							{sortedFilteredSessions.map((session) =>
-								renderSessionWithWorktrees(session, 'flat', { keyPrefix: 'flat' })
-							)}
-						</div>
+						/* FLAT LIST - No groups exist yet, show sessions directly with New Group button */
+						<>
+							<div className="flex flex-col">
+								{sortedFilteredSessions.map((session) =>
+									renderSessionWithWorktrees(session, 'flat', { keyPrefix: 'flat' })
+								)}
+							</div>
+							<div className="mt-4 px-3">
+								<button
+									onClick={createNewGroup}
+									className="w-full px-2 py-1.5 rounded-full text-[10px] font-medium hover:opacity-80 transition-opacity flex items-center justify-center gap-1"
+									style={{
+										backgroundColor: theme.colors.accent + '20',
+										color: theme.colors.accent,
+										border: `1px solid ${theme.colors.accent}40`,
+									}}
+									title="Create new group"
+								>
+									<Plus className="w-3 h-3" />
+									<span>New Group</span>
+								</button>
+							</div>
+						</>
 					) : groups.length > 0 && ungroupedSessions.length > 0 ? (
 						/* UNGROUPED FOLDER - Groups exist and there are ungrouped agents */
 						<div className="mb-1 mt-4">
@@ -2667,6 +2684,22 @@ function SessionListInner(props: SessionListProps) {
 									<Folder className="w-3.5 h-3.5" />
 									<span>Ungrouped Agents</span>
 								</div>
+								<button
+									onClick={(e) => {
+										e.stopPropagation();
+										createNewGroup();
+									}}
+									className="px-2 py-0.5 rounded-full text-[10px] font-medium hover:opacity-80 transition-opacity flex items-center gap-1"
+									style={{
+										backgroundColor: theme.colors.accent + '20',
+										color: theme.colors.accent,
+										border: `1px solid ${theme.colors.accent}40`,
+									}}
+									title="Create new group"
+								>
+									<Plus className="w-3 h-3" />
+									<span>New Group</span>
+								</button>
 							</div>
 
 							{!ungroupedCollapsed ? (
@@ -2692,25 +2725,25 @@ function SessionListInner(props: SessionListProps) {
 								</div>
 							)}
 						</div>
+					) : groups.length > 0 ? (
+						/* NO UNGROUPED AGENTS - Show standalone New Group button */
+						<div className="mt-4 px-3">
+							<button
+								onClick={createNewGroup}
+								className="w-full px-2 py-1.5 rounded-full text-[10px] font-medium hover:opacity-80 transition-opacity flex items-center justify-center gap-1"
+								style={{
+									backgroundColor: theme.colors.accent + '20',
+									color: theme.colors.accent,
+									border: `1px solid ${theme.colors.accent}40`,
+								}}
+								title="Create new group"
+							>
+								<Plus className="w-3 h-3" />
+								<span>New Group</span>
+							</button>
+						</div>
 					) : null}
 
-					{/* NEW GROUP BUTTON - Always visible */}
-					<div className="mt-4 px-3">
-						<button
-							onClick={createNewGroup}
-							className="w-full px-2 py-1.5 rounded-full text-[10px] font-medium hover:opacity-80 transition-opacity flex items-center justify-center gap-1"
-							style={{
-								backgroundColor: theme.colors.accent + '20',
-								color: theme.colors.accent,
-								border: `1px solid ${theme.colors.accent}40`,
-							}}
-							title="Create new group"
-						>
-							<Plus className="w-3 h-3" />
-							<span>New Group</span>
-						</button>
-					</div>
-
 					{/* Flexible spacer to push group chats to bottom */}
 					<div className="flex-grow min-h-4" />