diff --git a/crates/pinakes-server/src/dto/media.rs b/crates/pinakes-server/src/dto/media.rs
index 800f951..231bbb9 100644
--- a/crates/pinakes-server/src/dto/media.rs
+++ b/crates/pinakes-server/src/dto/media.rs
@@ -1,9 +1,39 @@
-use std::{collections::HashMap, path::PathBuf};
+use std::{
+  collections::HashMap,
+  path::{Path, PathBuf},
+};
 
 use chrono::{DateTime, Utc};
 use serde::{Deserialize, Serialize};
 use uuid::Uuid;
 
+/// Strip the longest matching root prefix from `full_path`, returning a
+/// forward-slash-separated relative path string. Falls back to the full path
+/// string when no root matches. If `roots` is empty, returns the full path as a
+/// string so internal callers that have not yet migrated still work.
+pub fn relativize_path(full_path: &Path, roots: &[PathBuf]) -> String {
+  let mut best: Option<&PathBuf> = None;
+  for root in roots {
+    if full_path.starts_with(root) {
+      let is_longer = best.map_or(true, |b| root.components().count() > b.components().count());
+      if is_longer {
+        best = Some(root);
+      }
+    }
+  }
+  if let Some(root) = best {
+    if let Ok(rel) = full_path.strip_prefix(root) {
+      // Normalise to forward slashes on all platforms.
+      return rel
+        .components()
+        .map(|c| c.as_os_str().to_string_lossy())
+        .collect::<Vec<_>>()
+        .join("/");
+    }
+  }
+  full_path.to_string_lossy().into_owned()
+}
+
 #[derive(Debug, Serialize)]
 pub struct MediaResponse {
   pub id:            String,
@@ -233,12 +263,18 @@ impl From<pinakes_core::model::ManagedStorageStats>
   }
 }
 
-// Conversion helpers
-impl From<pinakes_core::model::MediaItem> for MediaResponse {
-  fn from(item: pinakes_core::model::MediaItem) -> Self {
+impl MediaResponse {
+  /// Build a `MediaResponse` from a `MediaItem`, stripping the longest
+  /// matching root prefix from the path before serialization. Pass the
+  /// configured root directories so that clients receive a relative path
+  /// (e.g. `"Music/song.mp3"`) rather than a full server filesystem path.
+  pub fn new(
+    item: pinakes_core::model::MediaItem,
+    roots: &[PathBuf],
+  ) -> Self {
     Self {
       id:            item.id.0.to_string(),
-      path:          item.path.to_string_lossy().to_string(),
+      path:          relativize_path(&item.path, roots),
       file_name:     item.file_name,
       media_type:    serde_json::to_value(item.media_type)
         .ok()
@@ -282,6 +318,60 @@ impl From<pinakes_core::model::MediaItem> for MediaResponse {
   }
 }
 
+// Conversion helpers
+impl From<pinakes_core::model::MediaItem> for MediaResponse {
+  /// Convert using no root stripping. Prefer `MediaResponse::new(item, roots)`
+  /// at route-handler call sites where roots are available.
+  fn from(item: pinakes_core::model::MediaItem) -> Self {
+    Self::new(item, &[])
+  }
+}
+
+#[cfg(test)]
+mod tests {
+  use super::*;
+
+  #[test]
+  fn relativize_path_strips_matching_root() {
+    let roots = vec![PathBuf::from("/home/user/music")];
+    let path = Path::new("/home/user/music/artist/song.mp3");
+    assert_eq!(relativize_path(path, &roots), "artist/song.mp3");
+  }
+
+  #[test]
+  fn relativize_path_picks_longest_root() {
+    let roots = vec![
+      PathBuf::from("/home/user"),
+      PathBuf::from("/home/user/music"),
+    ];
+    let path = Path::new("/home/user/music/song.mp3");
+    assert_eq!(relativize_path(path, &roots), "song.mp3");
+  }
+
+  #[test]
+  fn relativize_path_no_match_returns_full() {
+    let roots = vec![PathBuf::from("/home/user/music")];
+    let path = Path::new("/srv/videos/movie.mkv");
+    assert_eq!(relativize_path(path, &roots), "/srv/videos/movie.mkv");
+  }
+
+  #[test]
+  fn relativize_path_empty_roots_returns_full() {
+    let path = Path::new("/home/user/music/song.mp3");
+    assert_eq!(
+      relativize_path(path, &[]),
+      "/home/user/music/song.mp3"
+    );
+  }
+
+  #[test]
+  fn relativize_path_exact_root_match() {
+    let roots = vec![PathBuf::from("/media/library")];
+    let path = Path::new("/media/library/file.mp3");
+    assert_eq!(relativize_path(path, &roots), "file.mp3");
+  }
+}
+
 // Watch progress
 #[derive(Debug, Deserialize)]
 pub struct WatchProgressRequest {
diff --git a/crates/pinakes-server/src/routes/analytics.rs b/crates/pinakes-server/src/routes/analytics.rs
index 19a3ef0..1698061 100644
--- a/crates/pinakes-server/src/routes/analytics.rs
+++ b/crates/pinakes-server/src/routes/analytics.rs
@@ -30,12 +30,13 @@ pub async fn get_most_viewed(
 ) -> Result<Json<Vec<MostViewedResponse>>, ApiError> {
   let limit = params.limit.unwrap_or(20).min(MAX_LIMIT);
   let results = state.storage.get_most_viewed(limit).await?;
+  let roots = state.config.read().await.directories.roots.clone();
   Ok(Json(
     results
       .into_iter()
       .map(|(item, count)| {
         MostViewedResponse {
-          media:      MediaResponse::from(item),
+          media:      MediaResponse::new(item, &roots),
           view_count: count,
         }
       })
@@ -51,7 +52,13 @@ pub async fn get_recently_viewed(
   let user_id = resolve_user_id(&state.storage, &username).await?;
   let limit = params.limit.unwrap_or(20).min(MAX_LIMIT);
   let items = state.storage.get_recently_viewed(user_id, limit).await?;
-  Ok(Json(items.into_iter().map(MediaResponse::from).collect()))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(
+    items
+      .into_iter()
+      .map(|item| MediaResponse::new(item, &roots))
+      .collect(),
+  ))
 }
 
 pub async fn record_event(
diff --git a/crates/pinakes-server/src/routes/books.rs b/crates/pinakes-server/src/routes/books.rs
index f513d9c..7ae042f 100644
--- a/crates/pinakes-server/src/routes/books.rs
+++ b/crates/pinakes-server/src/routes/books.rs
@@ -194,8 +194,9 @@ pub async fn list_books(
     )
     .await?;
 
+  let roots = state.config.read().await.directories.roots.clone();
   let response: Vec<MediaResponse> =
-    items.into_iter().map(MediaResponse::from).collect();
+    items.into_iter().map(|item| MediaResponse::new(item, &roots)).collect();
   Ok(Json(response))
 }
 
@@ -223,8 +224,9 @@ pub async fn get_series_books(
   Path(series_name): Path<String>,
 ) -> Result<impl IntoResponse, ApiError> {
   let items = state.storage.get_series_books(&series_name).await?;
+  let roots = state.config.read().await.directories.roots.clone();
   let response: Vec<MediaResponse> =
-    items.into_iter().map(MediaResponse::from).collect();
+    items.into_iter().map(|item| MediaResponse::new(item, &roots)).collect();
   Ok(Json(response))
 }
 
@@ -258,8 +260,9 @@ pub async fn get_author_books(
     .search_books(None, Some(&author_name), None, None, None, &pagination)
     .await?;
 
+  let roots = state.config.read().await.directories.roots.clone();
   let response: Vec<MediaResponse> =
-    items.into_iter().map(MediaResponse::from).collect();
+    items.into_iter().map(|item| MediaResponse::new(item, &roots)).collect();
   Ok(Json(response))
 }
 
@@ -317,8 +320,9 @@ pub async fn get_reading_list(
     .get_reading_list(user_id.0, params.status)
     .await?;
 
+  let roots = state.config.read().await.directories.roots.clone();
   let response: Vec<MediaResponse> =
-    items.into_iter().map(MediaResponse::from).collect();
+    items.into_iter().map(|item| MediaResponse::new(item, &roots)).collect();
   Ok(Json(response))
 }
 
diff --git a/crates/pinakes-server/src/routes/collections.rs b/crates/pinakes-server/src/routes/collections.rs
index 159d125..c746fa8 100644
--- a/crates/pinakes-server/src/routes/collections.rs
+++ b/crates/pinakes-server/src/routes/collections.rs
@@ -126,5 +126,11 @@ pub async fn get_members(
   let items =
     pinakes_core::collections::get_members(&state.storage, collection_id)
       .await?;
-  Ok(Json(items.into_iter().map(MediaResponse::from).collect()))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(
+    items
+      .into_iter()
+      .map(|item| MediaResponse::new(item, &roots))
+      .collect(),
+  ))
 }
diff --git a/crates/pinakes-server/src/routes/duplicates.rs b/crates/pinakes-server/src/routes/duplicates.rs
index 4da2ac8..075b3cc 100644
--- a/crates/pinakes-server/src/routes/duplicates.rs
+++ b/crates/pinakes-server/src/routes/duplicates.rs
@@ -10,6 +10,7 @@ pub async fn list_duplicates(
   State(state): State<AppState>,
 ) -> Result<Json<Vec<DuplicateGroupResponse>>, ApiError> {
   let groups = state.storage.find_duplicates().await?;
+  let roots = state.config.read().await.directories.roots.clone();
 
   let response: Vec<DuplicateGroupResponse> = groups
     .into_iter()
@@ -18,8 +19,10 @@ pub async fn list_duplicates(
         .first()
         .map(|i| i.content_hash.0.clone())
         .unwrap_or_default();
-      let media_items: Vec<MediaResponse> =
-        items.into_iter().map(MediaResponse::from).collect();
+      let media_items: Vec<MediaResponse> = items
+        .into_iter()
+        .map(|item| MediaResponse::new(item, &roots))
+        .collect();
       DuplicateGroupResponse {
         content_hash,
         items: media_items,
diff --git a/crates/pinakes-server/src/routes/media.rs b/crates/pinakes-server/src/routes/media.rs
index a2b3a4a..358db29 100644
--- a/crates/pinakes-server/src/routes/media.rs
+++ b/crates/pinakes-server/src/routes/media.rs
@@ -120,7 +120,13 @@ pub async fn list_media(
     params.sort,
   );
   let items = state.storage.list_media(&pagination).await?;
-  Ok(Json(items.into_iter().map(MediaResponse::from).collect()))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(
+    items
+      .into_iter()
+      .map(|item| MediaResponse::new(item, &roots))
+      .collect(),
+  ))
 }
 
 pub async fn get_media(
@@ -128,7 +134,8 @@ pub async fn get_media(
   Path(id): Path<Uuid>,
 ) -> Result<Json<MediaResponse>, ApiError> {
   let item = state.storage.get_media(MediaId(id)).await?;
-  Ok(Json(MediaResponse::from(item)))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(MediaResponse::new(item, &roots)))
 }
 
 /// Maximum length for short text fields (title, artist, album, genre).
@@ -206,7 +213,8 @@ pub async fn update_media(
     &serde_json::json!({"media_id": item.id.to_string()}),
   );
 
-  Ok(Json(MediaResponse::from(item)))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(MediaResponse::new(item, &roots)))
 }
 
 pub async fn delete_media(
@@ -574,12 +582,14 @@ pub async fn preview_directory(
     }
   }
 
+  let roots_for_walk = roots.clone();
   let files: Vec<DirectoryPreviewFile> =
     tokio::task::spawn_blocking(move || {
       let mut result = Vec::new();
       fn walk_dir(
         dir: &std::path::Path,
         recursive: bool,
+        roots: &[std::path::PathBuf],
         result: &mut Vec<DirectoryPreviewFile>,
       ) {
         let Ok(entries) = std::fs::read_dir(dir) else {
@@ -596,7 +606,7 @@ pub async fn preview_directory(
           }
           if path.is_dir() {
             if recursive {
-              walk_dir(&path, recursive, result);
+              walk_dir(&path, recursive, roots, result);
             }
           } else if path.is_file()
             && let Some(mt) =
@@ -612,7 +622,7 @@ pub async fn preview_directory(
               .and_then(|v| v.as_str().map(String::from))
               .unwrap_or_default();
             result.push(DirectoryPreviewFile {
-              path: path.to_string_lossy().to_string(),
+              path: crate::dto::relativize_path(&path, roots),
               file_name,
               media_type,
               file_size: size,
@@ -620,7 +630,7 @@ pub async fn preview_directory(
           }
         }
       }
-      walk_dir(&dir, recursive, &mut result);
+      walk_dir(&dir, recursive, &roots_for_walk, &mut result);
       result
     })
     .await
@@ -948,7 +958,8 @@ pub async fn rename_media(
   )
   .await?;
 
-  Ok(Json(MediaResponse::from(item)))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(MediaResponse::new(item, &roots)))
 }
 
 pub async fn move_media_endpoint(
@@ -994,7 +1005,8 @@ pub async fn move_media_endpoint(
   )
   .await?;
 
-  Ok(Json(MediaResponse::from(item)))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(MediaResponse::new(item, &roots)))
 }
 
 pub async fn batch_move_media(
@@ -1144,7 +1156,8 @@ pub async fn restore_media(
     &serde_json::json!({"media_id": media_id.to_string(), "restored": true}),
   );
 
-  Ok(Json(MediaResponse::from(item)))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(MediaResponse::new(item, &roots)))
 }
 
 pub async fn list_trash(
@@ -1159,9 +1172,13 @@ pub async fn list_trash(
 
   let items = state.storage.list_trash(&pagination).await?;
   let count = state.storage.count_trash().await?;
+  let roots = state.config.read().await.directories.roots.clone();
 
   Ok(Json(TrashResponse {
-    items:       items.into_iter().map(MediaResponse::from).collect(),
+    items:       items
+      .into_iter()
+      .map(|item| MediaResponse::new(item, &roots))
+      .collect(),
     total_count: count,
   }))
 }
diff --git a/crates/pinakes-server/src/routes/photos.rs b/crates/pinakes-server/src/routes/photos.rs
index edf04b6..4119774 100644
--- a/crates/pinakes-server/src/routes/photos.rs
+++ b/crates/pinakes-server/src/routes/photos.rs
@@ -121,13 +121,16 @@ pub async fn get_timeline(
   }
 
   // Convert to response format
+  let roots = state.config.read().await.directories.roots.clone();
   let mut timeline: Vec<TimelineGroup> = groups
     .into_iter()
     .map(|(date, items)| {
       let cover_id = items.first().map(|i| i.id.0.to_string());
       let count = items.len();
-      let items: Vec<MediaResponse> =
-        items.into_iter().map(MediaResponse::from).collect();
+      let items: Vec<MediaResponse> = items
+        .into_iter()
+        .map(|item| MediaResponse::new(item, &roots))
+        .collect();
 
       TimelineGroup {
         date,
diff --git a/crates/pinakes-server/src/routes/playlists.rs b/crates/pinakes-server/src/routes/playlists.rs
index 15df830..f341458 100644
--- a/crates/pinakes-server/src/routes/playlists.rs
+++ b/crates/pinakes-server/src/routes/playlists.rs
@@ -21,8 +21,10 @@ use crate::{
 
 /// Check whether a user has access to a playlist.
 ///
-/// * `require_write` – when `true` only the playlist owner is allowed (for
-///   mutations such as update, delete, add/remove/reorder items).  When `false`
+/// # Arguments
+///
+/// * `require_write` - when `true` only the playlist owner is allowed (for
+///   mutations such as update, delete, add/remove/reorder items). When `false`
 ///   the playlist must either be public or owned by the requesting user.
 async fn check_playlist_access(
   storage: &pinakes_core::storage::DynStorageBackend,
@@ -185,7 +187,13 @@ pub async fn list_items(
   let user_id = resolve_user_id(&state.storage, &username).await?;
   check_playlist_access(&state.storage, id, user_id, false).await?;
   let items = state.storage.get_playlist_items(id).await?;
-  Ok(Json(items.into_iter().map(MediaResponse::from).collect()))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(
+    items
+      .into_iter()
+      .map(|item| MediaResponse::new(item, &roots))
+      .collect(),
+  ))
 }
 
 pub async fn reorder_item(
@@ -213,5 +221,11 @@ pub async fn shuffle_playlist(
   use rand::seq::SliceRandom;
   let mut items = state.storage.get_playlist_items(id).await?;
   items.shuffle(&mut rand::rng());
-  Ok(Json(items.into_iter().map(MediaResponse::from).collect()))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(
+    items
+      .into_iter()
+      .map(|item| MediaResponse::new(item, &roots))
+      .collect(),
+  ))
 }
diff --git a/crates/pinakes-server/src/routes/search.rs b/crates/pinakes-server/src/routes/search.rs
index 3201047..7f0e6b1 100644
--- a/crates/pinakes-server/src/routes/search.rs
+++ b/crates/pinakes-server/src/routes/search.rs
@@ -51,9 +51,14 @@ pub async fn search(
   };
 
   let results = state.storage.search(&request).await?;
+  let roots = state.config.read().await.directories.roots.clone();
 
   Ok(Json(SearchResponse {
-    items:       results.items.into_iter().map(MediaResponse::from).collect(),
+    items:       results
+      .items
+      .into_iter()
+      .map(|item| MediaResponse::new(item, &roots))
+      .collect(),
     total_count: results.total_count,
   }))
 }
@@ -84,9 +89,14 @@ pub async fn search_post(
   };
 
   let results = state.storage.search(&request).await?;
+  let roots = state.config.read().await.directories.roots.clone();
 
   Ok(Json(SearchResponse {
-    items:       results.items.into_iter().map(MediaResponse::from).collect(),
+    items:       results
+      .items
+      .into_iter()
+      .map(|item| MediaResponse::new(item, &roots))
+      .collect(),
     total_count: results.total_count,
   }))
 }
diff --git a/crates/pinakes-server/src/routes/shares.rs b/crates/pinakes-server/src/routes/shares.rs
index 06b7e6d..76fea3c 100644
--- a/crates/pinakes-server/src/routes/shares.rs
+++ b/crates/pinakes-server/src/routes/shares.rs
@@ -506,6 +506,7 @@ pub async fn access_shared(
   let _ = state.storage.record_share_activity(&activity).await;
 
   // Return the shared content
+  let roots = state.config.read().await.directories.roots.clone();
   match &share.target {
     ShareTarget::Media { media_id } => {
       let item = state
@@ -514,8 +515,8 @@ pub async fn access_shared(
         .await
         .map_err(|e| ApiError::not_found(format!("Media not found: {e}")))?;
 
-      Ok(Json(SharedContentResponse::Single(MediaResponse::from(
-        item,
+      Ok(Json(SharedContentResponse::Single(MediaResponse::new(
+        item, &roots,
       ))))
     },
     ShareTarget::Collection { collection_id } => {
@@ -527,8 +528,10 @@ pub async fn access_shared(
           ApiError::not_found(format!("Collection not found: {e}"))
         })?;
 
-      let items: Vec<MediaResponse> =
-        members.into_iter().map(MediaResponse::from).collect();
+      let items: Vec<MediaResponse> = members
+        .into_iter()
+        .map(|item| MediaResponse::new(item, &roots))
+        .collect();
 
       Ok(Json(SharedContentResponse::Multiple { items }))
     },
@@ -553,8 +556,11 @@ pub async fn access_shared(
         .await
         .map_err(|e| ApiError::internal(format!("Search failed: {e}")))?;
 
-      let items: Vec<MediaResponse> =
-        results.items.into_iter().map(MediaResponse::from).collect();
+      let items: Vec<MediaResponse> = results
+        .items
+        .into_iter()
+        .map(|item| MediaResponse::new(item, &roots))
+        .collect();
 
       Ok(Json(SharedContentResponse::Multiple { items }))
     },
@@ -585,8 +591,11 @@ pub async fn access_shared(
         .await
         .map_err(|e| ApiError::internal(format!("Search failed: {e}")))?;
 
-      let items: Vec<MediaResponse> =
-        results.items.into_iter().map(MediaResponse::from).collect();
+      let items: Vec<MediaResponse> = results
+        .items
+        .into_iter()
+        .map(|item| MediaResponse::new(item, &roots))
+        .collect();
 
       Ok(Json(SharedContentResponse::Multiple { items }))
     },
diff --git a/crates/pinakes-server/src/routes/social.rs b/crates/pinakes-server/src/routes/social.rs
index b270ae0..f5bc17a 100644
--- a/crates/pinakes-server/src/routes/social.rs
+++ b/crates/pinakes-server/src/routes/social.rs
@@ -125,7 +125,13 @@ pub async fn list_favorites(
     .storage
     .get_user_favorites(user_id, &Pagination::default())
     .await?;
-  Ok(Json(items.into_iter().map(MediaResponse::from).collect()))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(
+    items
+      .into_iter()
+      .map(|item| MediaResponse::new(item, &roots))
+      .collect(),
+  ))
 }
 
 pub async fn create_share_link(
@@ -205,5 +211,6 @@ pub async fn access_shared_media(
   }
   state.storage.increment_share_views(&token).await?;
   let item = state.storage.get_media(link.media_id).await?;
-  Ok(Json(MediaResponse::from(item)))
+  let roots = state.config.read().await.directories.roots.clone();
+  Ok(Json(MediaResponse::new(item, &roots)))
 }