diff --git a/Cargo.lock b/Cargo.lock
index 9e4a577..fa6f289 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1324,7 +1324,7 @@ checksum = "5e5032e24019045c762d3c0f28f5b6b8bbf38563a65908389bf7978758920897"
 
 [[package]]
 name = "lore"
-version = "0.9.4"
+version = "0.9.5"
 dependencies = [
  "asupersync",
  "async-stream",
diff --git a/Cargo.toml b/Cargo.toml
index 93441eb..9bb8f7a 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -1,6 +1,6 @@
 [package]
 name = "lore"
-version = "0.9.4"
+version = "0.9.5"
 edition = "2024"
 description = "Gitlore - Local GitLab data management with semantic search"
 authors = ["Taylor Eernisse"]
diff --git a/src/core/ollama_mgmt.rs b/src/core/ollama_mgmt.rs
index 4a53185..2f350dd 100644
--- a/src/core/ollama_mgmt.rs
+++ b/src/core/ollama_mgmt.rs
@@ -47,14 +47,34 @@ fn is_local_url(base_url: &str) -> bool {
 
 // ── Detection (sync, fast) ──
 
-/// Check if the `ollama` binary is on PATH. Returns the path if found.
+/// Find the `ollama` binary. Checks PATH first, then well-known install
+/// locations as fallback (cron jobs have a minimal PATH that typically
+/// excludes Homebrew and other user-installed paths).
 pub fn find_ollama_binary() -> Option<PathBuf> {
-    Command::new("which")
+    // Try PATH first (works in interactive shells)
+    let from_path = Command::new("which")
         .arg("ollama")
         .output()
         .ok()
         .filter(|o| o.status.success())
-        .map(|o| PathBuf::from(String::from_utf8_lossy(&o.stdout).trim().to_string()))
+        .map(|o| PathBuf::from(String::from_utf8_lossy(&o.stdout).trim().to_string()));
+
+    if from_path.is_some() {
+        return from_path;
+    }
+
+    // Fallback: check well-known locations (for cron/launchd contexts)
+    const WELL_KNOWN: &[&str] = &[
+        "/opt/homebrew/bin/ollama",  // macOS Apple Silicon (Homebrew)
+        "/usr/local/bin/ollama",     // macOS Intel (Homebrew) / Linux manual
+        "/usr/bin/ollama",           // Linux package manager
+        "/snap/bin/ollama",          // Linux Snap
+    ];
+
+    WELL_KNOWN
+        .iter()
+        .map(PathBuf::from)
+        .find(|p| p.is_file())
 }
 
 /// Quick sync check: can we TCP-connect to Ollama's HTTP port?
@@ -118,9 +138,9 @@ pub fn ensure_ollama(base_url: &str) -> OllamaEnsureResult {
     let is_local = is_local_url(base_url);
 
     // Step 1: Is the binary installed? (only relevant for local)
-    if is_local {
-        let installed = find_ollama_binary().is_some();
-        if !installed {
+    let binary_path = if is_local {
+        let path = find_ollama_binary();
+        if path.is_none() {
             return OllamaEnsureResult {
                 installed: false,
                 was_running: false,
@@ -130,7 +150,10 @@ pub fn ensure_ollama(base_url: &str) -> OllamaEnsureResult {
                 install_hint: Some(install_instructions().to_string()),
             };
         }
-    }
+        path
+    } else {
+        None
+    };
 
     // Step 2: Already running?
     if is_ollama_reachable(base_url) {
@@ -158,8 +181,11 @@ pub fn ensure_ollama(base_url: &str) -> OllamaEnsureResult {
         };
     }
 
-    // Step 4: Try to start it (local only)
-    let spawn_result = Command::new("ollama")
+    // Step 4: Try to start it (local only, using discovered absolute path)
+    // Using the absolute path is critical — cron has a minimal PATH that
+    // typically excludes Homebrew and other user-installed locations.
+    let ollama_bin = binary_path.expect("binary_path is Some for local URLs after step 1");
+    let spawn_result = Command::new(&ollama_bin)
         .arg("serve")
         .stdout(std::process::Stdio::null())
         .stderr(std::process::Stdio::null())