diff --git a/src/service/media.rs b/src/service/media.rs
index 399dc1dd..f5dfda4d 100644
--- a/src/service/media.rs
+++ b/src/service/media.rs
@@ -8,7 +8,7 @@ use tokio::{
 };
 use tracing::{debug, warn};
 
-use crate::{services, Result};
+use crate::{services, utils, Result};
 
 mod data;
 
@@ -114,14 +114,29 @@ impl Service {
     /// Deletes a media object and all associated thumbnails.
     #[tracing::instrument(skip(self))]
     pub(crate) async fn delete(&self, mxc: OwnedMxcUri) -> Result<()> {
-        let (_, key) = self.db.search_file_metadata(mxc.clone(), 0, 0)?;
+        let (_, key) =
+            self.db.search_file_metadata(mxc.clone(), 0, 0).inspect_err(
+                |error| warn!(%error, "Failed to find original media key"),
+            )?;
 
         let thumbnails = self.db.search_thumbnails_metadata(mxc)?;
         for (_, thumbnail_key) in thumbnails {
-            self.delete_by_key(thumbnail_key).await?;
+            self.delete_by_key(thumbnail_key.clone()).await.inspect_err(
+                |error| {
+                    warn!(
+                        thumbnail_key = utils::u8_slice_to_hex(
+                            thumbnail_key.as_bytes()
+                        ),
+                        %error,
+                        "Failed to delete thumbnail media"
+                    );
+                },
+            )?;
         }
 
-        self.delete_by_key(key).await?;
+        self.delete_by_key(key).await.inspect_err(
+            |error| warn!(%error, "Failed to delete original media"),
+        )?;
 
         Ok(())
     }