diff --git a/scripts/hooks/session-start.js b/scripts/hooks/session-start.js
index a9943080..c95881ff 100644
--- a/scripts/hooks/session-start.js
+++ b/scripts/hooks/session-start.js
@@ -13,6 +13,7 @@ const {
   getSessionsDir,
   getSessionSearchDirs,
   getLearnedSkillsDir,
+  getProjectName,
   findFiles,
   ensureDir,
   readFile,
@@ -23,6 +24,25 @@ const { getPackageManager, getSelectionPrompt } = require('../lib/package-manage
 const { listAliases } = require('../lib/session-aliases');
 const { detectProjectType } = require('../lib/project-detect');
 const path = require('path');
+const fs = require('fs');
+
+/**
+ * Resolve a filesystem path to its canonical (real) form.
+ *
+ * Handles symlinks and, on case-insensitive filesystems (macOS, Windows),
+ * normalizes casing so that path comparisons are reliable.
+ * Falls back to the original path if resolution fails (e.g. path no longer exists).
+ *
+ * @param {string} p - The path to normalize.
+ * @returns {string} The canonical path, or the original if resolution fails.
+ */
+function normalizePath(p) {
+  try {
+    return fs.realpathSync(p);
+  } catch {
+    return p;
+  }
+}
 
 function dedupeRecentSessions(searchDirs) {
   const recentSessionsByName = new Map();
@@ -53,6 +73,87 @@ function dedupeRecentSessions(searchDirs) {
     .sort((left, right) => right.mtime - left.mtime || left.dirIndex - right.dirIndex);
 }
 
+/**
+ * Select the best matching session for the current working directory.
+ *
+ * Session files written by session-end.js contain header fields like:
+ *   **Project:** my-project
+ *   **Worktree:** /path/to/project
+ *
+ * This function reads each session file once, caching its content, and
+ * returns both the selected session object and its already-read content
+ * to avoid duplicate I/O in the caller.
+ *
+ * Priority (highest to lowest):
+ *   1. Exact worktree (cwd) match — most recent
+ *   2. Same project name match — most recent
+ *   3. Fallback to overall most recent (original behavior)
+ *
+ * Sessions are already sorted newest-first, so the first match in each
+ * category wins.
+ *
+ * @param {Array<Object>} sessions - Deduplicated session list, sorted newest-first.
+ * @param {string} cwd - Current working directory (process.cwd()).
+ * @param {string} currentProject - Current project name from getProjectName().
+ * @returns {{ session: Object, content: string, matchReason: string } | null}
+ *   The best matching session with its cached content and match reason,
+ *   or null if the sessions array is empty or all files are unreadable.
+ */
+function selectMatchingSession(sessions, cwd, currentProject) {
+  if (sessions.length === 0) return null;
+
+  // Normalize cwd once outside the loop to avoid repeated syscalls
+  const normalizedCwd = normalizePath(cwd);
+
+  let projectMatch = null;
+  let projectMatchContent = null;
+  let fallbackSession = null;
+  let fallbackContent = null;
+
+  for (const session of sessions) {
+    const content = readFile(session.path);
+    if (!content) continue;
+
+    // Cache first readable session+content pair for fallback
+    if (!fallbackSession) {
+      fallbackSession = session;
+      fallbackContent = content;
+    }
+
+    // Extract **Worktree:** field
+    const worktreeMatch = content.match(/\*\*Worktree:\*\*\s*(.+)$/m);
+    const sessionWorktree = worktreeMatch ? worktreeMatch[1].trim() : '';
+
+    // Exact worktree match — best possible, return immediately
+    // Normalize both paths to handle symlinks and case-insensitive filesystems
+    if (sessionWorktree && normalizePath(sessionWorktree) === normalizedCwd) {
+      return { session, content, matchReason: 'worktree' };
+    }
+
+    // Project name match — keep searching for a worktree match
+    if (!projectMatch && currentProject) {
+      const projectFieldMatch = content.match(/\*\*Project:\*\*\s*(.+)$/m);
+      const sessionProject = projectFieldMatch ? projectFieldMatch[1].trim() : '';
+      if (sessionProject && sessionProject === currentProject) {
+        projectMatch = session;
+        projectMatchContent = content;
+      }
+    }
+  }
+
+  if (projectMatch) {
+    return { session: projectMatch, content: projectMatchContent, matchReason: 'project' };
+  }
+
+  // Fallback: most recent readable session (original behavior)
+  if (fallbackSession) {
+    return { session: fallbackSession, content: fallbackContent, matchReason: 'recency-fallback' };
+  }
+
+  log('[SessionStart] All session files were unreadable');
+  return null;
+}
+
 async function main() {
   const sessionsDir = getSessionsDir();
   const learnedDir = getLearnedSkillsDir();
@@ -66,15 +167,26 @@ async function main() {
   const recentSessions = dedupeRecentSessions(getSessionSearchDirs());
 
   if (recentSessions.length > 0) {
-    const latest = recentSessions[0];
     log(`[SessionStart] Found ${recentSessions.length} recent session(s)`);
-    log(`[SessionStart] Latest: ${latest.path}`);
 
-    // Read and inject the latest session content into Claude's context
-    const content = stripAnsi(readFile(latest.path));
-    if (content && !content.includes('[Session context goes here]')) {
-      // Only inject if the session has actual content (not the blank template)
-      additionalContextParts.push(`Previous session summary:\n${content}`);
+    // Prefer a session that matches the current working directory or project.
+    // Session files contain **Project:** and **Worktree:** header fields written
+    // by session-end.js, so we can match against them.
+    const cwd = process.cwd();
+    const currentProject = getProjectName() || '';
+
+    const result = selectMatchingSession(recentSessions, cwd, currentProject);
+
+    if (result) {
+      log(`[SessionStart] Selected: ${result.session.path} (match: ${result.matchReason})`);
+
+      // Use the already-read content from selectMatchingSession (no duplicate I/O)
+      const content = stripAnsi(result.content);
+      if (content && !content.includes('[Session context goes here]')) {
+        additionalContextParts.push(`Previous session summary:\n${content}`);
+      }
+    } else {
+      log('[SessionStart] No matching session found');
     }
   }