diff --git a/crates/cli/src/main.rs b/crates/cli/src/main.rs
index d42de9d..de35382 100644
--- a/crates/cli/src/main.rs
+++ b/crates/cli/src/main.rs
@@ -1423,8 +1423,15 @@ struct AuditResult {
 struct AuditFileResult {
     file: String,
     bytes: usize,
+    /// A file is considered matched if wagl already has a file-memory item with `source:<path>`.
     matched: bool,
     matched_id: Option<String>,
+    /// Current file content hash (normalized).
+    file_hash: String,
+    /// Stored item content hash (normalized), if a match was found.
+    stored_hash: Option<String>,
+    /// True if a matched file's current content differs from the stored item text.
+    drifted: bool,
 }
 
 fn collect_memory_files(root: &Path) -> anyhow::Result<Vec<PathBuf>> {
@@ -1450,22 +1457,59 @@ fn collect_memory_files(root: &Path) -> anyhow::Result<Vec<PathBuf>> {
 fn audit_files(root: &Path, files: &[PathBuf], items: &[MemoryItem]) -> AuditResult {
     let mut results = Vec::new();
     let mut matched = 0;
+
+    fn audit_norm(s: &str) -> &str {
+        // Normalize for file-memory matching.
+        // Treat trailing whitespace/newlines as non-semantic to avoid duplicate imports
+        // when editors add/remove a final newline.
+        s.trim_end()
+    }
+
+    fn blake3_hex(s: &str) -> String {
+        blake3::hash(s.as_bytes()).to_hex().to_string()
+    }
+
     for path in files {
         let content = std::fs::read_to_string(path).unwrap_or_default();
         let bytes = content.len();
-        let matched_item = items
+
+        let file_hash = blake3_hex(audit_norm(&content));
+
+        let src_tag = format!("source:{}", path.display());
+        let matched_id = items
             .iter()
-            .find(|item| item.text == content)
+            .find(|item| {
+                item.tags.iter().any(|t| t == "file-memory")
+                    && item.tags.iter().any(|t| t == &src_tag)
+            })
             .map(|item| item.id.clone());
-        let is_match = matched_item.is_some();
+
+        let is_match = matched_id.is_some();
         if is_match {
             matched += 1;
         }
+
+        let stored_hash = matched_id.as_deref().and_then(|id| {
+            items
+                .iter()
+                .find(|item| item.id == id)
+                .map(|item| blake3_hex(audit_norm(&item.text)))
+        });
+
+        // If we matched by source tag, check whether content drifted (e.g., file edited).
+        let drifted = stored_hash
+            .as_deref()
+            .map(|h| h != file_hash.as_str())
+            .unwrap_or(false);
+
         results.push(AuditFileResult {
             file: path.display().to_string(),
             bytes,
             matched: is_match,
-            matched_id: matched_item,
+            matched_id,
+            file_hash,
+            stored_hash,
+            drifted,
         });
     }
 
@@ -1489,9 +1533,17 @@ async fn import_missing_files(db: &MemoryDb, audit: &AuditResult) -> anyhow::Res
         if content.trim().is_empty() {
             continue;
         }
+
+        // Include a stable content hash tag to aid future dedupe/debugging.
+        // (Normalization matches audit behavior: ignore trailing whitespace.)
+        let content_hash = blake3::hash(content.trim_end().as_bytes())
+            .to_hex()
+            .to_string();
+
         let tags = vec![
             "file-memory".to_string(),
             format!("source:{}", path.display()),
+            format!("contenthash:blake3:{}", content_hash),
         ];
         let item = MemoryItem {
             id: uuid::Uuid::new_v4().to_string(),