diff --git a/imessage-database/src/tables/attachment.rs b/imessage-database/src/tables/attachment.rs
index 71da5c4a..fd8e4ec0 100644
--- a/imessage-database/src/tables/attachment.rs
+++ b/imessage-database/src/tables/attachment.rs
@@ -251,7 +251,7 @@ impl Attachment {
     /// Generate a MacOS path for an attachment
     fn gen_macos_attachment(path: &str) -> String {
         if path.starts_with('~') {
-            return path.replace('~', &home());
+            return path.replacen('~', &home(), 1);
         }
         path.to_string()
     }
@@ -390,6 +390,18 @@ mod tests {
         );
     }
 
+    #[test]
+    fn can_get_resolved_path_macos_raw_tilde() {
+        let db_path = PathBuf::from("fake_root");
+        let mut attachment = sample_attachment();
+        attachment.filename = Some("~/a/b/c~d.png".to_string());
+
+        assert!(attachment
+            .resolved_attachment_path(&Platform::MacOS, &db_path)
+            .unwrap()
+            .ends_with("c~d.png"));
+    }
+
     #[test]
     fn can_get_resolved_path_ios() {
         let db_path = PathBuf::from("fake_root");