diff --git a/tests/e2e/markdown-editor.test.e2e.ts b/tests/e2e/markdown-editor.test.e2e.ts
index c2d4057bc9..ae79b75800 100644
--- a/tests/e2e/markdown-editor.test.e2e.ts
+++ b/tests/e2e/markdown-editor.test.e2e.ts
@@ -196,6 +196,13 @@ test('markdown indentation with Tab', async ({page}) => {
   await textarea.pressSequentially('  ');
   await textarea.press('Shift+Tab');
   await expect(textarea).toHaveValue(initText);
+
+  // Check that indentation tokens not at the start of the string do not interrupt indentation
+  await textarea.focus();
+  await textarea.fill(initText);
+  await textarea.pressSequentially(tab);
+  await textarea.press('Tab');
+  await expect(textarea).toHaveValue(`* first\n* second\n* third\n    * last    `);
 });
 
 test('markdown block quote indentation', async ({page}) => {
diff --git a/web_src/js/features/comp/ComboMarkdownEditor.js b/web_src/js/features/comp/ComboMarkdownEditor.js
index 37544bf10f..8c010ae386 100644
--- a/web_src/js/features/comp/ComboMarkdownEditor.js
+++ b/web_src/js/features/comp/ComboMarkdownEditor.js
@@ -476,7 +476,23 @@ class ComboMarkdownEditor {
     // Indent with 4 spaces, unindent 4 spaces or fewer or a lost tab.
     const indentPrefix = '    ';
     const unindentRegex = /^( {1,4}|\t|> {0,4})/;
-    const indentLevel = / {4}|\t|> /g;
+    const indentTokens = ['    ', '\t', '> '];
+
+    const indentLevel = (line) => {
+      let indent = 0;
+      let matchingToken;
+
+      do {
+        matchingToken = indentTokens.find((token) => line.startsWith(token));
+
+        if (matchingToken) {
+          indent++;
+          line = line.substr(matchingToken.length);
+        }
+      } while (matchingToken);
+
+      return indent;
+    };
 
     const value = this.textarea.value;
     const lines = value.split('\n');
@@ -525,8 +541,8 @@ class ComboMarkdownEditor {
       const match = line.match(listPrefixRegex);
       if (!match || !match[0].length) return false;
       // Check that the line isn't already indented in relation to parent.
-      const levels = line.match(indentLevel)?.length ?? 0;
-      const parentLevels = !firstLineIdx ? 0 : lines[firstLineIdx - 1].match(indentLevel)?.length ?? 0;
+      const levels = indentLevel(line);
+      const parentLevels = firstLineIdx > 0 ? indentLevel(lines.at(firstLineIdx - 1)) : 0;
       // Quotes can *begin* multiple levels in, so just allow whatever for now.
       if (levels - parentLevels > 0 && !isQuote) return false;
     }