diff --git a/e2e_tests/docx-tools/test_search_docx_files_content.py b/e2e_tests/docx-tools/test_search_docx_files_content.py
new file mode 100644
index 0000000000..bcf8bd752b
--- /dev/null
+++ b/e2e_tests/docx-tools/test_search_docx_files_content.py
@@ -0,0 +1,85 @@
+import os
+import re
+import shutil
+import zipfile
+import pytest
+from docx import Document
+
+user_input = input("\nEnter search terms separated by commas (e.g. \\\sqrt, \\\pi): ")
+# Process the input into a list and clean up whitespace
+PATT_LIST = [item.strip() for item in user_input.split(",")]
+
+
+def test_search_docx_files_content():
+    base_to_dir = f"{os.getcwd()}/docx_search"
+
+    # Ensure the destination directory exists
+    if os.path.exists(base_to_dir):
+        shutil.rmtree(base_to_dir)
+    os.makedirs(base_to_dir)
+
+    home_dir = os.path.expanduser("~")
+    base_from_dir = f"{home_dir}/Downloads/"
+
+    all_files = os.listdir(base_from_dir)
+
+    files = [
+        x
+        for x in all_files
+        if x.startswith("openstax-osbooks")
+        and x.lower().endswith(".zip")
+        and not os.path.isdir(os.path.join(base_from_dir, x))
+    ]
+
+    unzip_dirs = []
+
+    if len(files) > 0:
+        for f_name in files:
+            file_source = os.path.join(base_from_dir, f_name)
+            file_dest = os.path.join(base_to_dir, f_name)
+
+            shutil.copy(file_source, file_dest)
+            # Use the directory containing the zip for extraction
+            unzip_dirs.append(base_to_dir)
+    else:
+        pytest.fail(f"No zip files found in {base_from_dir}")
+
+    # Deduplicate directory list and unzip
+    for j in set(unzip_dirs):
+        for file in os.listdir(j):
+            file_path = os.path.join(j, file)
+            if zipfile.is_zipfile(file_path):
+                with zipfile.ZipFile(file_path) as item:
+                    # Extract into a folder named after the zip
+                    extract_path = os.path.join(j, file.replace(".zip", ""))
+                    item.extractall(extract_path)
+                os.remove(file_path)
+
+    found_anything = False
+
+    # 1. Combine PATT_LIST into a single regex for speed: "term1|term2|term3"
+    combined_pattern = "|".join(PATT_LIST)
+
+    for root, _, filenames in os.walk(base_to_dir):
+        docx_files = [
+            f for f in filenames if f.endswith(".docx") and not f.startswith("~$")
+        ]
+
+        for filename in docx_files:
+            f_path = os.path.join(root, filename)
+            doc = Document(f_path)
+
+            # Check every paragraph against the combined regex
+            for para in doc.paragraphs:
+                match = re.search(combined_pattern, para.text)
+                if match:
+                    found_anything = True
+                    # match.group() tells us exactly which keyword was found
+                    print(
+                        f"\nFOUND '{match.group()}': {para.text} \nLOCATION: {f_path}"
+                    )
+
+    if not found_anything:
+        print(
+            f"\n{'=' * 60}\nSEARCH COMPLETE: No matches found for {PATT_LIST}\n{'=' * 60}"
+        )