diff --git a/src/project.rs b/src/project.rs
index 4d29c72a..16c3a7cf 100644
--- a/src/project.rs
+++ b/src/project.rs
@@ -111,8 +111,13 @@ impl Project {
     pub fn load_from_slice(
         contents: &[u8],
         project_file_location: &Path,
-    ) -> Result<Self, serde_json::Error> {
-        let mut project: Self = serde_json::from_slice(&contents)?;
+    ) -> Result<Self, ProjectError> {
+        let mut project: Self =
+            serde_json::from_slice(&contents).map_err(|source| Error::Json {
+                source,
+                path: project_file_location.to_owned(),
+            })?;
+
         project.file_location = project_file_location.to_path_buf();
         project.check_compatibility();
         Ok(project)
diff --git a/src/serve_session.rs b/src/serve_session.rs
index 1164dc5a..d43d4981 100644
--- a/src/serve_session.rs
+++ b/src/serve_session.rs
@@ -1,11 +1,14 @@
 use std::{
+    borrow::Cow,
     collections::HashSet,
+    io,
     path::{Path, PathBuf},
     sync::{Arc, Mutex, MutexGuard},
     time::Instant,
 };
 
 use crossbeam_channel::Sender;
+use memofs::IoResultExt;
 use memofs::Vfs;
 use rbx_dom_weak::RbxInstanceProperties;
 use thiserror::Error;
@@ -97,11 +100,23 @@ impl ServeSession {
 
         log::trace!("Starting new ServeSession at path {}", start_path.display());
 
-        log::debug!("Loading project file from {}", start_path.display());
-        let root_project =
-            Project::load_fuzzy(start_path)?.ok_or_else(|| ServeSessionError::NoProjectFound {
-                path: start_path.to_owned(),
-            })?;
+        let project_path;
+        if Project::is_project_file(start_path) {
+            project_path = Cow::Borrowed(start_path);
+        } else {
+            project_path = Cow::Owned(start_path.join("default.project.json"));
+        }
+
+        log::debug!("Loading project file from {}", project_path.display());
+
+        let root_project = match vfs.read(&project_path).with_not_found()? {
+            Some(contents) => Project::load_from_slice(&contents, &project_path)?,
+            None => {
+                return Err(ServeSessionError::NoProjectFound {
+                    path: project_path.to_path_buf(),
+                });
+            }
+        };
 
         let mut tree = RojoTree::new(InstancePropertiesWithMeta {
             properties: RbxInstanceProperties {
@@ -206,6 +221,12 @@ pub enum ServeSessionError {
     )]
     NoProjectFound { path: PathBuf },
 
+    #[error(transparent)]
+    Io {
+        #[from]
+        source: io::Error,
+    },
+
     #[error(transparent)]
     Project {
         #[from]
diff --git a/src/snapshot_middleware/error.rs b/src/snapshot_middleware/error.rs
index a1c1665d..7e0e3847 100644
--- a/src/snapshot_middleware/error.rs
+++ b/src/snapshot_middleware/error.rs
@@ -2,6 +2,8 @@ use std::{io, path::PathBuf};
 
 use thiserror::Error;
 
+use crate::project::ProjectError;
+
 #[derive(Debug, Error)]
 pub enum SnapshotError {
     #[error("file name had malformed Unicode")]
@@ -14,10 +16,7 @@ pub enum SnapshotError {
     },
 
     #[error("malformed project file at path {}", .path.display())]
-    MalformedProject {
-        source: serde_json::Error,
-        path: PathBuf,
-    },
+    MalformedProject { source: ProjectError, path: PathBuf },
 
     #[error("malformed .model.json file at path {}", .path.display())]
     MalformedModelJson {
@@ -62,7 +61,7 @@ impl SnapshotError {
         }
     }
 
-    pub(crate) fn malformed_project(source: serde_json::Error, path: impl Into<PathBuf>) -> Self {
+    pub(crate) fn malformed_project(source: ProjectError, path: impl Into<PathBuf>) -> Self {
         Self::MalformedProject {
             source,
             path: path.into(),