Convert Thousands of DOCX Files into One AZW3 (with Tappable TOC)

[hfdt]

Hi, all.

I do at least one page of journaling in Microsoft Word every day, and sometimes I find it interesting / grounding to re-read past journal entries, and I would like to do that re-reading on my Kindle Paperwhite. I've managed to get several entries onto the device using Calibre; that's not a problem. What I'm looking to do now is this:

I want one AZW3 file with ALL these old journal entries in it, and I want it to have a tappable TOC with a link to each entry.

The thing is, I've been doing this for a long time, and I have over eight thousand individual .docx files that would need to be incorporated. A friend suggested I convert the pile of .docx files into one giant PDF and then convert the PDF into AZW3, because when you combine files in Acrobat, it bookmarks each separate file automatically unless you tell it not to. I tried this, but I could not find a way to parlay those bookmarks into a TOC in Calibre - and in any case, I've since read that PDF is not ideal as a starting format.

Any ideas how I can get from a pile of .docx files to one massive AZW3 with a tappable TOC?

Thanks in advance.

[BetterRed]

I would use Word's Insert->Object->Object and/or Text File tools to create a merged DOCX and convert that to AZW3.



You may need to adjust the Convert->Structure->XPath…



…to get the ToC you want.

BR

[kovidgoyal]

convert them to epub and use the epubmerge plugin and then convert the rsulting merged epub to azw3.

[PeterT]

You could even convert all the files to ePub at the command line using ebook-convert, and then use epubmerge plugin to combine them all.

[BetterRed]

Just for fun I asked ChatGPT, "How to Concatenate Multiple DOCX Files with File Names as Headers". Here's the response.

To concatenate multiple DOCX files and insert each file’s name as a header before its content, you can do this manually in Microsoft Word or automate it using a script.

⚙️ Automated Method (Using Python + python-docx)
If you have many files, automation is your friend. Here’s a Python script that does the job:

from docx import Document
import os

def merge_docs_with_headers(folder_path, output_path):
    merged_doc = Document()

    for filename in sorted(os.listdir(folder_path)):
        if filename.endswith(".docx"):
            file_path = os.path.join(folder_path, filename)
            doc = Document(file_path)

            # Add file name as a heading
            merged_doc.add_heading(filename, level=1)

            # Append content
            for element in doc.element.body:
                merged_doc.element.body.append(element)

    merged_doc.save(output_path)

# Example usage
merge_docs_with_headers("path/to/your/docx/files", "merged_output.docx")

This script:
- Loops through all .docx files in a folder.
- Adds each file’s name as a heading.
- Appends the content of each file to the master document.
You’ll need to install the python-docx library if you haven’t already: pip install python-docx

BR