diff --git a/src/web/public/session-ui.js b/src/web/public/session-ui.js
index 99ad73cd..63747a91 100644
--- a/src/web/public/session-ui.js
+++ b/src/web/public/session-ui.js
@@ -489,23 +489,55 @@ Object.assign(CodemanApp.prototype, {
         const date = new Date(s.lastModified);
         const timeStr = date.toLocaleDateString('en', { month: 'short', day: 'numeric' })
           + ' ' + date.toLocaleTimeString('en', { hour: '2-digit', minute: '2-digit', hour12: false });
-        const shortDir = s.workingDir.replace(/^\/home\/[^/]+\//, '~/');
+        // Abbreviate the home prefix. This used to match `/home/<user>/` only, so
+        // on macOS (`/Users/<user>/`) nothing was stripped and every row spent its
+        // first ~19 characters on an identical prefix — with the tail ellipsized,
+        // all rows rendered as `/Users/jordanryan/co…` and became indistinguishable.
+        const shortDir = s.workingDir.replace(/^\/(?:home|Users)\/[^/]+\//, '~/');
+        // Lead with the folder that identifies the row; the parent path trails and
+        // is what gets truncated. Truncation must never eat the identity.
+        const lastSlash = shortDir.lastIndexOf('/');
+        const leafName = lastSlash === -1 ? shortDir : shortDir.slice(lastSlash + 1);
+        // `<repo>/.claude/worktrees` in the parent path is pure noise once the pill
+        // says which worktree it is — drop it so the repo stays visible instead.
+        const parentDir = (lastSlash === -1 ? '' : shortDir.slice(0, lastSlash)).replace(/\/\.claude\/worktrees$/, '');
 
         const btn = document.createElement('button');
-        btn.className = 'run-mode-option';
+        btn.className = 'run-mode-option run-mode-hist-row';
         btn.title = s.workingDir;
         btn.dataset.sessionId = s.sessionId;
         btn.dataset.workingDir = s.workingDir;
 
-        const dirSpan = document.createElement('span');
-        dirSpan.className = 'hist-dir';
-        dirSpan.textContent = shortDir;
+        const nameSpan = document.createElement('span');
+        nameSpan.className = 'hist-name';
+        nameSpan.textContent = leafName;
+
+        const parts = [nameSpan];
+
+        // Worktree pill, same data the session rows use (#266). A worktree's
+        // directory basename is often just the worktree name, so without this two
+        // worktrees of one repo still read alike.
+        const wt = this._worktreeLabel ? this._worktreeLabel(s) : '';
+        if (wt) {
+          const wtSpan = document.createElement('span');
+          wtSpan.className = 'hist-wt';
+          wtSpan.textContent = wt;
+          parts.push(wtSpan);
+        }
+
+        if (parentDir) {
+          const dirSpan = document.createElement('span');
+          dirSpan.className = 'hist-dir';
+          dirSpan.textContent = parentDir;
+          parts.push(dirSpan);
+        }
 
         const metaSpan = document.createElement('span');
         metaSpan.className = 'hist-meta';
         metaSpan.textContent = timeStr;
+        parts.push(metaSpan);
 
-        btn.append(dirSpan, metaSpan);
+        btn.append(...parts);
         btn.addEventListener('click', (e) => {
           e.stopPropagation();
           this.resumeHistorySession(s.sessionId, s.workingDir, s.name);
diff --git a/src/web/public/styles.css b/src/web/public/styles.css
index 47c199ad..c283cd5c 100644
--- a/src/web/public/styles.css
+++ b/src/web/public/styles.css
@@ -4392,6 +4392,24 @@ body.touch-device .terminal-container .xterm .xterm-helper-textarea {
   max-width: 250px;
   box-shadow: 0 8px 32px rgba(0, 0, 0, 0.5), 0 2px 8px rgba(0, 0, 0, 0.3);
 }
+
+/* Above phone width the menu becomes a full-width drawer across the bottom of the
+   window. The 250px cap above was sized for a `~/<dir>/<repo>` row, which assumed
+   the home prefix had been abbreviated — it never was on macOS, so real rows blew
+   straight through it and ellipsized into `/Users/<user>/co…`, identical on every
+   line. Width is what buys room for the worktree + branch, so the cap is lifted
+   rather than nudged. Phones keep the compact popover: mobile.css positions this
+   menu itself and a viewport-wide drawer there would cover the composer. */
+@media (min-width: 769px) {
+  .run-mode-menu {
+    max-width: none;
+    width: calc(100vw - 24px);
+  }
+  .run-mode-history {
+    /* More rows are worth showing once each one is legible. */
+    max-height: 320px;
+  }
+}
 .run-mode-menu.active {
   display: flex;
   flex-direction: column;
@@ -4462,6 +4480,31 @@ body.touch-device .terminal-container .xterm .xterm-helper-textarea {
 .run-mode-history .run-mode-option {
   max-width: 100%;
 }
+/* Recent-session row: identity first, path last.
+   The row reads  <folder>  [⑂ worktree · branch]  <parent path>  <time>
+   with only the parent path allowed to shrink, so truncation can never hide
+   which project (or which worktree) a row refers to. */
+.run-mode-hist-row {
+  align-items: baseline;
+  gap: 8px;
+}
+.run-mode-option .hist-name {
+  flex: 0 1 auto;
+  min-width: 0;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+  font-weight: 600;
+}
+.run-mode-option .hist-wt {
+  flex: 0 0 auto;
+  font-size: 0.78em;
+  padding: 0 5px;
+  border-radius: 3px;
+  background: color-mix(in srgb, var(--accent) 16%, transparent);
+  color: var(--accent);
+  white-space: nowrap;
+}
 .run-mode-option .hist-dir {
   flex: 1;
   /* A flex item's default min-width is auto, so without this the path refuses to
@@ -4471,6 +4514,11 @@ body.touch-device .terminal-container .xterm .xterm-helper-textarea {
   overflow: hidden;
   text-overflow: ellipsis;
   white-space: nowrap;
+  /* The parent path is context, not identity — dim it and let it be the part
+     that loses characters first. */
+  color: var(--text-muted);
+  font-size: 0.85em;
+  text-align: right;
 }
 .run-mode-option .hist-meta {
   font-size: 0.85em;