diff --git a/crates/extension_host/src/extension_host.rs b/crates/extension_host/src/extension_host.rs
index 09e8259771668346c237c1cc05e6074ca3b37797..1f907f514d5c1ea6f5783c620c25b6b1370a158e 100644
--- a/crates/extension_host/src/extension_host.rs
+++ b/crates/extension_host/src/extension_host.rs
@@ -1534,12 +1534,14 @@ impl ExtensionStore {
         let is_dev = fs
             .metadata(&extension_dir)
             .await?
-            .context("directory does not exist")?
+            .with_context(|| format!("missing extension directory {extension_dir:?}"))?
             .is_symlink;
 
-        if let Ok(mut language_paths) = fs.read_dir(&extension_dir.join("languages")).await {
+        let language_dir = extension_dir.join("languages");
+        if let Ok(mut language_paths) = fs.read_dir(&language_dir).await {
             while let Some(language_path) = language_paths.next().await {
-                let language_path = language_path?;
+                let language_path = language_path
+                    .with_context(|| format!("reading entries in language dir {language_dir:?}"))?;
                 let Ok(relative_path) = language_path.strip_prefix(&extension_dir) else {
                     continue;
                 };
@@ -1549,7 +1551,10 @@ impl ExtensionStore {
                 if !fs_metadata.is_dir {
                     continue;
                 }
-                let config = fs.load(&language_path.join("config.toml")).await?;
+                let language_config_path = language_path.join("config.toml");
+                let config = fs.load(&language_config_path).await.with_context(|| {
+                    format!("loading language config from {language_config_path:?}")
+                })?;
                 let config = ::toml::from_str::<LanguageConfig>(&config)?;
 
                 let relative_path = relative_path.to_path_buf();