diff --git a/crates/path-cli/src/cmd_pathbase.rs b/crates/path-cli/src/cmd_pathbase.rs
index bfff3f7b..c824875b 100644
--- a/crates/path-cli/src/cmd_pathbase.rs
+++ b/crates/path-cli/src/cmd_pathbase.rs
@@ -349,10 +349,34 @@ fn block_on<F: std::future::Future>(f: F) -> F::Output {
 /// supplied. Progenitor doesn't expose a bearer-token setter, so we
 /// pre-bake the header into the http client and hand it via
 /// `Client::new_with_client`.
+/// How long any pathbase request may take.
+///
+/// One flat value covered every call, and 30s is a fine ceiling for the
+/// small ones — auth, listing repos, deleting a graph. It is the wrong
+/// ceiling for an upload: a long agent session derives to several MB, and
+/// the whole document goes up in one request. A real session hit this
+/// against a *loopback* server, which is the case that should never time
+/// out, and the error it produced — "request timed out after 30s — try
+/// again, or shrink the upload" — invites you to shrink a conversation
+/// that already happened.
+///
+/// So the default is generous and the value is settable. `PATH_HTTP_TIMEOUT_SECS`
+/// covers every command, including the ones with no flag of their own — which
+/// is what a launchd agent or a cron sweep can reach.
+pub(crate) fn http_timeout() -> std::time::Duration {
+    const DEFAULT_SECS: u64 = 300;
+    let secs = std::env::var("PATH_HTTP_TIMEOUT_SECS")
+        .ok()
+        .and_then(|s| s.trim().parse::<u64>().ok())
+        .filter(|s| *s > 0)
+        .unwrap_or(DEFAULT_SECS);
+    std::time::Duration::from_secs(secs)
+}
+
 fn pathbase_client(base_url: &str, token: Option<&str>) -> Result<pathbase_client::Client> {
     let mut builder = reqwest::Client::builder()
         .user_agent(concat!("path-cli/", env!("CARGO_PKG_VERSION")))
-        .timeout(std::time::Duration::from_secs(30));
+        .timeout(http_timeout());
     if let Some(t) = token {
         let mut headers = reqwest::header::HeaderMap::new();
         let mut auth = reqwest::header::HeaderValue::from_str(&format!("Bearer {t}"))
diff --git a/crates/path-cli/src/cmd_share.rs b/crates/path-cli/src/cmd_share.rs
index 0d6ba9c4..e1750bf4 100644
--- a/crates/path-cli/src/cmd_share.rs
+++ b/crates/path-cli/src/cmd_share.rs
@@ -57,6 +57,15 @@ pub struct ShareArgs {
     /// Skip writing the cache; derive in-memory only
     #[arg(long)]
     pub no_cache: bool,
+
+    /// Seconds to allow the upload before giving up (default 300).
+    ///
+    /// A long session derives to several MB and goes up in one request, so
+    /// the ceiling that suits every other call is the wrong one here. Sets
+    /// `PATH_HTTP_TIMEOUT_SECS` for this invocation; export that directly for
+    /// commands that have no flag, or for an agent that runs `share` for you.
+    #[arg(long, value_name = "SECS")]
+    pub timeout: Option<u64>,
 }
 
 /// One artifact surfaced by a provider — today always an agent session.
@@ -482,6 +491,15 @@ fn collect_cursor(
 }
 
 pub fn run(args: ShareArgs) -> Result<()> {
+    // Set before any client is built: `http_timeout` reads this, and every
+    // pathbase call in this process goes through one client constructor. Doing
+    // it here rather than threading a Duration keeps the eight call sites — all
+    // of them small requests that never needed a knob — untouched.
+    if let Some(secs) = args.timeout {
+        // SAFETY: single-threaded startup, before any client or task exists.
+        unsafe { std::env::set_var("PATH_HTTP_TIMEOUT_SECS", secs.to_string()) };
+    }
+
     let harness = args.harness.map(|h| h.artifact_type());
 
     if args.session.is_some() && harness.is_none() {
@@ -579,6 +597,9 @@ pub fn run(args: ShareArgs) -> Result<()> {
             None
         },
         no_cache: args.no_cache,
+        // Already applied to the environment by `run`, so this is only carried
+        // for completeness — the picker path uploads through the same client.
+        timeout: args.timeout,
     };
     // Show the conversation title in the confirmation line; the session id
     // is opaque and doesn't help the user verify they picked the right
@@ -1408,6 +1429,11 @@ mod tests {
             session: None,
             project: None,
             no_cache: false,
+            // `run` applies this to the environment before any client exists,
+            // so it is never read on this path; None keeps these tests on the
+            // default timeout rather than asserting against a knob they do not
+            // exercise.
+            timeout: None,
         }
     }