diff --git a/server/commands/documentImporter.ts b/server/commands/documentImporter.ts
index 46ba48b46..53554e6f9 100644
--- a/server/commands/documentImporter.ts
+++ b/server/commands/documentImporter.ts
@@ -179,7 +179,6 @@ async function documentImporter({
 
   let title = fileName.replace(/\.[^/.]+$/, "");
   let text = await fileInfo.getMarkdown(content);
-  text = text.trim();
 
   // find and extract emoji near the beginning of the document.
   const regex = emojiRegex();
@@ -191,17 +190,18 @@ async function documentImporter({
 
   // If the first line of the imported text looks like a markdown heading
   // then we can use this as the document title rather than the file name.
-  if (text.startsWith("# ")) {
+  if (text.trim().startsWith("# ")) {
     const result = parseTitle(text);
     title = result.title;
     text = text
+      .trim()
       .replace(new RegExp(`#\\s+${escapeRegExp(title)}`), "")
       .trimStart();
   }
 
   // Replace any <br> generated by the turndown plugin with escaped newlines
   // to match our hardbreak parser.
-  text = text.replace(/<br>/gi, "\\n");
+  text = text.trim().replace(/<br>/gi, "\\n");
 
   text = await DocumentHelper.replaceImagesWithAttachments(
     text,