diff --git a/Cargo.lock b/Cargo.lock
index 7f29534..af0753a 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1951,6 +1951,7 @@ dependencies = [
  "jotdown",
  "log",
  "rand",
+ "rayon",
  "regex",
  "serde",
  "serde_json",
diff --git a/crates/treehouse/Cargo.toml b/crates/treehouse/Cargo.toml
index 08f278c..c74bbb0 100644
--- a/crates/treehouse/Cargo.toml
+++ b/crates/treehouse/Cargo.toml
@@ -25,6 +25,7 @@ indexmap = { version = "2.2.6", features = ["serde"] }
 jotdown = { version = "0.4.1", default-features = false }
 log = { workspace = true }
 rand = "0.8.5"
+rayon = "1.10.0"
 regex = "1.10.3"
 serde = { version = "1.0.183", features = ["derive"] }
 serde_json = "1.0.105"
diff --git a/crates/treehouse/src/generate.rs b/crates/treehouse/src/generate.rs
index 21bc43f..614057a 100644
--- a/crates/treehouse/src/generate.rs
+++ b/crates/treehouse/src/generate.rs
@@ -514,7 +514,9 @@ pub fn target(dirs: Arc<Dirs>, sources: Arc<Sources>) -> DynDir {
 
     let dir_index = DirIndex::new(sources.parsed_trees.keys().map(|x| &**x));
     let tree_view = TreehouseDir::new(dirs, sources, dir_index);
+
     let tree_view = ContentCache::new(tree_view);
+    tree_view.warm_up();
     let tree_view = HtmlCanonicalize::new(tree_view);
 
     Overlay::new(tree_view.to_dyn(), root.to_dyn()).to_dyn()
diff --git a/crates/treehouse/src/vfs/content_cache.rs b/crates/treehouse/src/vfs/content_cache.rs
index 8c4a44a..ae7e16d 100644
--- a/crates/treehouse/src/vfs/content_cache.rs
+++ b/crates/treehouse/src/vfs/content_cache.rs
@@ -1,8 +1,13 @@
-use std::fmt::{self, Debug};
+use std::{
+    fmt::{self, Debug},
+    ops::ControlFlow,
+};
 
 use dashmap::DashMap;
+use log::debug;
+use rayon::iter::{IntoParallelRefIterator, ParallelIterator};
 
-use super::{Dir, DirEntry, EditPath, ImageSize, VPath, VPathBuf};
+use super::{walk_dir_rec, Dir, DirEntry, EditPath, ImageSize, VPath, VPathBuf};
 
 pub struct ContentCache<T> {
     inner: T,
@@ -18,6 +23,22 @@ impl<T> ContentCache<T> {
     }
 }
 
+impl<T> ContentCache<T>
+where
+    T: Dir + Send + Sync,
+{
+    pub fn warm_up(&self) {
+        debug!("warm_up({self:?})");
+        let mut paths = vec![];
+        walk_dir_rec(&self.inner, VPath::ROOT, &mut |path| {
+            paths.push(path.to_owned());
+            ControlFlow::Continue(())
+        });
+
+        paths.par_iter().for_each(|path| _ = self.content(path));
+    }
+}
+
 impl<T> Dir for ContentCache<T>
 where
     T: Dir,
diff --git a/crates/treehouse/src/vfs/path.rs b/crates/treehouse/src/vfs/path.rs
index 6d9707f..baec51a 100644
--- a/crates/treehouse/src/vfs/path.rs
+++ b/crates/treehouse/src/vfs/path.rs
@@ -91,10 +91,16 @@ impl VPath {
     }
 
     pub fn segments(&self) -> impl Iterator<Item = &Self> {
-        self.as_str().split(Self::SEPARATOR).map(|s| unsafe {
-            // SAFETY: Since we're splitting on the separator, the path cannot start or end with it.
-            Self::new_unchecked(s)
-        })
+        if self.is_root() {
+            None.into_iter().flatten()
+        } else {
+            Some(self.as_str().split(Self::SEPARATOR).map(|s| unsafe {
+                // SAFETY: Since we're splitting on the separator, the path cannot start or end with it.
+                Self::new_unchecked(s)
+            }))
+            .into_iter()
+            .flatten()
+        }
     }
 
     pub fn rsegments(&self) -> impl Iterator<Item = &Self> {
@@ -203,7 +209,9 @@ impl VPathBuf {
 
     pub fn push(&mut self, sub: &VPath) {
         if !sub.is_empty() {
-            self.path.push('/');
+            if !self.is_empty() {
+                self.path.push('/');
+            }
             self.path.push_str(&sub.path);
         }
     }