diff --git a/rslib/src/media/changetracker.rs b/rslib/src/media/changetracker.rs
index 8949ca67d..fde118384 100644
--- a/rslib/src/media/changetracker.rs
+++ b/rslib/src/media/changetracker.rs
@@ -4,7 +4,8 @@
 use crate::err::{AnkiError, Result};
 use crate::media::database::{MediaDatabaseContext, MediaEntry};
 use crate::media::files::{
-    mtime_as_i64, sha1_of_file, MEDIA_SYNC_FILESIZE_LIMIT, NONSYNCABLE_FILENAME,
+    filename_if_normalized, mtime_as_i64, sha1_of_file, MEDIA_SYNC_FILESIZE_LIMIT,
+    NONSYNCABLE_FILENAME,
 };
 use std::collections::HashMap;
 use std::path::Path;
@@ -78,10 +79,6 @@ where
 
     /// Scan through the media folder, finding changes.
     /// Returns (added/changed files, removed files).
-    ///
-    /// Checks for invalid filenames and unicode normalization are deferred
-    /// until syncing time, as we can't trust the entries previous Anki versions
-    /// wrote are correct.
     fn media_folder_changes(
         &mut self,
         mut mtimes: HashMap<String, i64>,
@@ -99,13 +96,22 @@ where
 
             // if the filename is not valid unicode, skip it
             let fname_os = dentry.file_name();
-            let fname = match fname_os.to_str() {
+            let disk_fname = match fname_os.to_str() {
                 Some(s) => s,
                 None => continue,
             };
 
+            // make sure the filename is normalized
+            let fname = match filename_if_normalized(&disk_fname) {
+                Some(fname) => fname,
+                None => {
+                    // not normalized; skip it
+                    continue;
+                }
+            };
+
             // ignore blacklisted files
-            if NONSYNCABLE_FILENAME.is_match(fname) {
+            if NONSYNCABLE_FILENAME.is_match(fname.as_ref()) {
                 continue;
             }
 
@@ -116,7 +122,7 @@ where
             }
 
             // remove from mtimes for later deletion tracking
-            let previous_mtime = mtimes.remove(fname);
+            let previous_mtime = mtimes.remove(fname.as_ref());
 
             // skip files that have not been modified
             let mtime = metadata
diff --git a/rslib/src/media/files.rs b/rslib/src/media/files.rs
index b6bd4d192..74cdc5fe4 100644
--- a/rslib/src/media/files.rs
+++ b/rslib/src/media/files.rs
@@ -71,19 +71,58 @@ pub(crate) fn normalize_filename(fname: &str) -> Cow<str> {
         output = output.chars().nfc().collect::<String>().into();
     }
 
-    if output.chars().any(disallowed_char) {
-        output = output.replace(disallowed_char, "").into()
+    normalize_nfc_filename(output)
+}
+
+/// See normalize_filename(). This function expects NFC-normalized input.
+fn normalize_nfc_filename(mut fname: Cow<str>) -> Cow<str> {
+    if fname.chars().any(disallowed_char) {
+        fname = fname.replace(disallowed_char, "").into()
     }
 
-    if let Cow::Owned(o) = WINDOWS_DEVICE_NAME.replace_all(output.as_ref(), "${1}_${2}") {
-        output = o.into();
+    if let Cow::Owned(o) = WINDOWS_DEVICE_NAME.replace_all(fname.as_ref(), "${1}_${2}") {
+        fname = o.into();
     }
 
-    if let Cow::Owned(o) = truncate_filename(output.as_ref(), MAX_FILENAME_LENGTH) {
-        output = o.into();
+    if let Cow::Owned(o) = truncate_filename(fname.as_ref(), MAX_FILENAME_LENGTH) {
+        fname = o.into();
     }
 
-    output
+    fname
+}
+
+/// Return the filename in NFC form if the filename is valid.
+///
+/// Returns None if the filename is not normalized
+/// (NFD, invalid chars, etc)
+///
+/// On Apple devices, the filename may be stored on disk in NFD encoding,
+/// but can be accessed as NFC. On these devices, if the filename
+/// is otherwise valid, the filename is returned as NFC.
+#[allow(clippy::collapsible_if)]
+pub(super) fn filename_if_normalized(fname: &str) -> Option<Cow<str>> {
+    if cfg!(target_vendor = "apple") {
+        if !is_nfc(fname) {
+            let as_nfc = fname.chars().nfc().collect::<String>();
+            if let Cow::Borrowed(_) = normalize_nfc_filename(as_nfc.as_str().into()) {
+                Some(as_nfc.into())
+            } else {
+                None
+            }
+        } else {
+            if let Cow::Borrowed(_) = normalize_nfc_filename(fname.into()) {
+                Some(fname.into())
+            } else {
+                None
+            }
+        }
+    } else {
+        if let Cow::Borrowed(_) = normalize_filename(fname) {
+            Some(fname.into())
+        } else {
+            None
+        }
+    }
 }
 
 /// Write desired_name into folder, renaming if existing file has different content.