diff --git a/cli/transbeam-cli b/cli/transbeam-cli
index ace59ae..411716f 100755
--- a/cli/transbeam-cli
+++ b/cli/transbeam-cli
@@ -65,11 +65,11 @@ async def file_loader(files):
                         file_progress.update(len(data))
                         yield data
 
-async def send(paths, host, password, lifetime, collection_name=None):
+async def send(paths, host, password, lifetime, collection_name=None, relpaths=False):
     paths = [path for path in paths if path.is_file()]
     fileMetadata = [
         {
-            "name": path.name,
+            "name": str(path) if relpaths else path.name,
             "size": path.stat().st_size,
             "modtime": math.floor(path.stat().st_mtime * 1000),
         } for path in paths
@@ -97,6 +97,7 @@ parser = argparse.ArgumentParser(description="Upload files to transbeam")
 parser.add_argument("-l", "--lifetime", type=int, default=7, help="Lifetime in days for files (default 7)")
 parser.add_argument("-H", "--host", type=str, default="transbeam.link", help="transbeam host (default transbeam.link)")
 parser.add_argument("-n", "--collection-name", type=str, help="Name for a collection of multiple files")
+parser.add_argument("-R", "--relative-paths", action="store_true", help="Preserve file paths relative to working directory")
 parser.add_argument("files", type=pathlib.Path, nargs="+", help="Files to upload")
 
 async def main():
@@ -105,6 +106,6 @@ async def main():
         print("--collection-name is only applicable when multiple files are being uploaded")
         exit(1)
     password = getpass.getpass()
-    await send(args.files, args.host, password, args.lifetime, args.collection_name)
+    await send(args.files, args.host, password, args.lifetime, args.collection_name, args.relative_paths)
 
 asyncio.run(main())
diff --git a/src/upload.rs b/src/upload.rs
index 4f59490..b016f6a 100644
--- a/src/upload.rs
+++ b/src/upload.rs
@@ -1,4 +1,4 @@
-use std::{collections::HashSet, fs::File, io::Write};
+use std::{collections::HashSet, fs::File, io::Write, path::Path, path::Component};
 
 use actix::{fut::future::ActorFutureExt, Actor, ActorContext, AsyncContext, StreamHandler};
 use actix_http::ws::{CloseReason, Item};
@@ -22,20 +22,42 @@ const MAX_FILES: usize = 256;
 const FILENAME_DATE_FORMAT: &[time::format_description::FormatItem] =
     time::macros::format_description!("[year]-[month]-[day]-[hour][minute][second]");
 
-/// Sanitises a filename after performing unicode normalization,
+/// Sanitises a file or directory name after performing unicode normalization,
 /// optionally reducing the length limit to leave space for an
 /// extension yet to be added.
-fn sanitise(name: &str, extension_length: usize) -> String {
+fn sanitise_path_component(name: &str, extension_length: usize) -> String {
     let name = name.nfd().collect::<String>();
     sanitise_with_options(
         &name,
         &SanOptions {
-            length_limit: SanOptions::DEFAULT.length_limit - extension_length,
+            length_limit: SanOptions::DEFAULT.length_limit.saturating_sub(extension_length),
             ..SanOptions::DEFAULT
         },
     )
 }
 
+fn sanitise_path(path: &str) -> String {
+    let mut san_path = Path::new(path).components().rfold(String::new(), |subpath, c| {
+        if subpath.len() >= SanOptions::DEFAULT.length_limit*8 {
+            return subpath;
+        }
+        if let Component::Normal(s) = c {
+            let mut component = sanitise_path_component(&s.to_string_lossy(), 0);
+            if !subpath.is_empty() {
+                component.push('/');
+                component.push_str(&subpath);
+            }
+            component
+        } else {
+            subpath
+        }
+    });
+    if san_path.is_empty() {
+        san_path.push('_');
+    }
+    san_path
+}
+
 #[derive(thiserror::Error, Debug)]
 enum Error {
     #[error("Failed to parse file metadata")]
@@ -114,7 +136,7 @@ pub use crate::state::v1::UploadedFile;
 impl UploadedFile {
     fn new(name: &str, size: u64, modtime: OffsetDateTime) -> Self {
         Self {
-            name: sanitise(name, 0),
+            name: sanitise_path(name),
             size,
             modtime,
         }
@@ -285,7 +307,7 @@ impl Uploader {
                         info!("Wrapping in zipfile generator");
                         let now = OffsetDateTime::now_utc();
                         let collection_name =
-                            collection_name.map(|f| sanitise(&f, 4)).unwrap_or_else(|| {
+                            collection_name.map(|f| sanitise_path_component(&f, 4)).unwrap_or_else(|| {
                                 super::APP_NAME.to_owned()
                                     + &now.format(FILENAME_DATE_FORMAT).unwrap()
                             });