Why Does Formatting Break After Converting Doc In Epub?

If you want a reliable, repeatable workflow I lean on a combination of Pandoc and a little manual cleanup — it’s saved me from font headaches more than once. First, save your .doc (or .docx) cleanly from Word: strip weird tracked changes, use simple styles for headings and body text, and bundle the fonts you want to embed into a folder. Then run Pandoc from the command line like this: pandoc mydoc.docx -o book.epub --epub-embed-font=/path/to/MyFont-Regular.ttf --epub-embed-font=/path/to/MyFont-Italic.ttf. Pandoc will generate an EPUB with the font files packaged and a CSS that references them. After that I always open the EPUB in Sigil (or Calibre’s editor) to check two things: that the fonts landed in the /fonts folder and that the stylesheet has @font-face rules pointing to those files. If needed I tweak the CSS to force font-family for headings/body. A couple of practical notes: embed only fonts you’re licensed to distribute, test on real devices (iBooks, Kobo, phone reader), and if you target Kindle you’ll need to convert to AZW3 with Calibre and verify fonts survive the conversion. This workflow gives me predictable results and lets me fine-tune typography without hunting through dozens of GUIs.

Okay, here's a clear path that worked for me the last time I turned a messy manuscript into a polished, clickable EPUB. First, clean up your DOC/DOCX: use Word's built-in heading styles (Heading 1, Heading 2, etc.) for chapter and section titles — converters detect those. Remove manual page numbering placeholders, unneeded headers/footers, and odd text boxes. Save as .docx. If you want a cover, prepare a JPG or PNG named cover.jpg. Then pick a tool. I like Pandoc for simplicity: pandoc -o book.epub book.docx --toc --toc-depth=2 --epub-cover-image=cover.jpg will produce an EPUB with a navigation (clickable TOC) derived from the headings. If you prefer a GUI, import the .docx into Calibre and use Convert books → EPUB, enabling chapter detection (Structure Detection or XPath expressions) so the TOC is generated from headings. After conversion, open the EPUB in Sigil or an e-reader to inspect the nav.xhtml/toc.ncx and tweak styling or metadata. Run epubcheck to validate, and test on several readers (phone app, Kindle Previewer, Adobe Digital Editions) to make sure TOC links behave the way you expect.

Trying to get a clean EPUB from a Word document? Calibre can absolutely do DOC/DOCX -> EPUB conversions and it can build a proper table of contents, but the trick is in how the source is structured and which detection options you use. In my experience, the simplest route is to save your manuscript as a clean .docx (avoid legacy .doc if possible), make sure you’ve used consistent heading styles for chapter titles (Heading 1 for main chapters, Heading 2 for sub-sections), and then let Calibre detect chapters based on those headings. That usually produces a solid TOC automatically. If the Word file is messy—manual bolded titles instead of styled headings—Calibre will struggle, so some tidy-up in Word pays off more than fiddling with conversion settings later. Here’s a practical workflow I use that almost always works: 1) In Word, apply Heading styles to every chapter title and remove odd manual page-break tricks. 2) Save as .docx (or even export as clean HTML if Word is being naughty). 3) Open Calibre, Add book, select it and hit Convert books -> EPUB. On the conversion dialog, click the 'Table of Contents' (or 'Structure detection' in older versions) section. You can choose to detect chapters by heading levels, by a regular expression, or by an XPath expression. For most novels, selecting heading detection (e.g., detect chapters by 'h1' or choose ‘Level 1 headings’) is enough. If your chapters start with the word 'Chapter' you can use a regex like ^Chapter\s+\d+ to catch them. Also check the options for inserting page breaks before chapter titles so each chapter starts cleanly in the resulting EPUB. If Calibre’s automatic detection doesn’t get you the TOC you want, there are a couple of easy fallbacks. First, try saving the Word doc as HTML and import that into Calibre—the HTML is often more predictable and keeps heading tags intact. Second, use Calibre’s built-in 'Edit book' after conversion to tweak the navigation file (nav.xhtml) or the NCX if you want full control of entries. For power users, the command line tool ebook-convert has flags to control TOC generation more granularly (like regex-based chapter detection and TOC thresholds). Another tip: if you see weird formatting in the EPUB viewer, clean the Word source of hidden bookmarks and tracked changes—those things trip up Calibre’s parser more than you’d expect. Bottom line: yes, Calibre can convert DOC/DOCX to EPUB with a working TOC, and it’s surprisingly flexible once you understand the detection options. I tend to spend twenty minutes cleaning headings and then let Calibre do the heavy lifting; the results are usually exactly what I want, and it feels great to flip through a neat TOC on my ereader.

If you're trying to turn a .doc or .docx into an EPUB on Windows, there are a bunch of great options depending on whether you want one-click convenience, command-line power, or fine-grained editing. I usually pick the tool based on how clean my source file is and how much post-conversion tweaking I expect to do. For simple, text-heavy manuscripts I reach for 'Pandoc' or 'Calibre'; when I need to polish the final ebook structure and hack the HTML/CSS, 'Sigil' and 'Calibre' become my best friends. If you prefer graphical, point-and-click programs, 'Jutoh' and online converters like CloudConvert or Convertio are solid picks too. 'Calibre' is probably the go-to for many people — it's free, Windows-friendly, and combines conversion, metadata editing, cover setting, and a device-friendly output all in one place. You can use the GUI (Add books -> Convert books -> choose EPUB) or its CLI: ebook-convert input.docx output.epub --cover cover.jpg. 'Pandoc' is my favorite when I want reproducible conversions and control from the terminal: pandoc MyBook.docx -o MyBook.epub --toc --metadata title=MyBook --epub-cover-image=cover.jpg. Pandoc handles styles and can use templates, producing clean EPUB3 if you set the right options. 'Sigil' is not a converter per se, but it's an excellent EPUB editor — I often run a conversion first, then open the EPUB in 'Sigil' to fix CSS, tweak the navigation, and ensure chapter splits are perfect. 'LibreOffice' can export to EPUB with the right extension (Writer2ePub) or with newer builds that include EPUB export, which is handy if you prefer staying inside a word processor. For paid/ polished solutions, 'Jutoh' makes book creation and formatting straightforward and includes features like project templates, TOC management, and easy cover import. Online converters like 'CloudConvert' or 'Convertio' are great for single files when you don't want to install anything — just be careful with sensitive content and double-check formatting after the conversion. A few extra tips from my own trial-and-error: convert to .docx first (if you have old .doc), use consistent Heading styles in the document so converters can auto-create a proper TOC, embed images at reasonable sizes, set metadata and a cover art before conversion, and always validate the result (Calibre’s ebook viewer or an EPUB validator like epubcheck). If something looks off, open the EPUB in 'Sigil' or re-run Pandoc with a template. My personal workflow is to clean up the manuscript in Word or LibreOffice, run 'Pandoc' for a quick, clean EPUB, then import into 'Calibre' for metadata and device-specific tweaks, and finally open in 'Sigil' if I need to hand-edit HTML/CSS. That combo gives me the speed of automated conversion plus the precision of manual editing when I need it — it feels satisfying turning a messy draft into something that reads like a real book.

I've collected a little toolkit over the years for validating and fixing EPUB metadata, so here’s what I do when a file looks suspicious. First, treat an EPUB like a zip archive: rename it to .zip or just unzip it and open META-INF/container.xml to find the rootfile (the package document, usually an .opf). That package document is where the metadata lives — dc:title, dc:creator, dc:identifier, dc:language, meta elements, etc. If you want to eyeball things quickly, Sigil or Calibre's editor are great: Sigil shows the package.opf in a friendly editor and highlights XPath-like structure, while Calibre’s 'Edit metadata' lets you change values and run quick sanity checks. For authoritative validation, I rely on epubcheck. It’s the industry standard: grab the latest epubcheck .jar from its GitHub repo (the project is maintained under the W3C umbrella) and run java -jar epubcheck.jar mybook.epub. It flags missing or malformed metadata (missing identifier, invalid language codes, bad xml:lang usage, duplicated identifiers, wrong cover declarations) and points to the specific location in the package document. If you prefer web UIs, there are online EPUB validator front-ends that use epubcheck under the hood — handy for a one-off without installing Java. When accessibility or metadata for assistive tech matters, I run ACE (the Accessibility Checker for EPUB) from DAISY — it highlights metadata issues related to accessibility metadata, roles, and resource declarations. For platform-specific quirks, Kindle Previewer can reveal conversion warnings that stem from metadata oddities (like bad date formats or nonstandard cover meta tags) and Smashwords/KDP often expect certain identifier formats or language settings. I also use command-line helpers: ebook-meta (from Calibre) to dump metadata quickly (ebook-meta mybook.epub), and xmllint or an XPath expression to validate values against patterns (ISO 639 language codes, valid UUIDs for identifiers, proper date formats). Practical tips from my messy archive: always ensure package document and container.xml are consistent, use one unique dc:identifier with opf:scheme or @id set, keep dc:language as an ISO code, and avoid sticking the cover in unsupported meta tags — use the manifest item with properties='cover-image' for EPUB3. If you want automation, add epubcheck to CI (GitHub Actions has examples) so every commit gets validated. I like the control of command-line checks but the GUI tools are friendlier for quick edits — both have saved me from ugly store rejections more times than I can count.

Okay, here’s how I usually do it when I want a clean EPUB that actually behaves on my Kindle. First I tidy the .doc or .docx in Word: apply Heading styles for chapters (Heading 1 for main, Heading 2 for sections), remove headers/footers, avoid manual tabs/spaces, and insert page breaks between chapters. Then I either use Word’s Export → Create EPUB option (if my Word has it) or save as .docx and open it in Calibre. In Calibre I import the file, edit metadata (title, author, cover), and convert to EPUB. From EPUB I open 'Kindle Previewer' and let it generate a KPF file — that’s what Kindle Direct Publishing prefers now, and Previewer will show you how it renders on different devices. Formatting tips: use simple fonts, optimize images (72–150 dpi, scale to 600–1000 px wide), check the generated table of contents (headings become the EPUB TOC), and validate with EPUBCheck if you want to be thorough. If you need to send something to your own Kindle, the Personal Document Service still works: email the .docx to your Kindle address with the word "convert" in the subject to get it into Kindle format. I usually do a quick test on Previewer and on an actual Kindle app before I consider it done — little fixes pop up that are easy to fix in the source document.

If you want a result that actually looks like the original document, the trick starts well before conversion: use consistent styles and a clean .docx. I always strip out manual formatting—no weird fonts, no direct color tweaks, and absolutely accept tracked changes or comments before exporting. Put headings in Heading 1/2/3 styles, use standard paragraph styles for body text, and replace complex Word-only elements (SmartArt, text boxes, equations) with images or simplified versions. Save as .docx (not .doc) because modern tools read .docx far better. From there, pick your tool depending on how faithful you need the layout. For most books I use a two-step approach: export to clean HTML (Word allows 'Save as Web Page, Filtered'), then open that HTML in an EPUB editor like Sigil or feed the .docx to Calibre/Pandoc. In the editor I tidy up the CSS, embed a cover and fonts if licensing allows, and build a proper navigation (NCX/TOC). If your document has complex page layouts (magazines, comics), consider fixed-layout EPUB or export to PDF instead. Always validate with epubcheck and test on a few readers (Calibre's viewer, Apple Books, a Kindle via conversion) — you’ll catch orphaned images, wrong line spacing, or broken TOC links that way. Little things like relative image paths, UTF-8 encoding, and clean metadata go a long way toward preserving formatting, and a quick pass editing the XHTML/CSS inside an EPUB editor often fixes what automatic converters miss.

If you want fonts to survive the trip into an ebook, here’s the practical workflow I swear by after a few frustrating exports. Embedding fonts in an EPUB is basically about three things: including the actual font files in the EPUB package, referencing them from a stylesheet using @font-face, and making sure the package manifest (content.opf) lists those files with correct media types. Before anything else, check the font’s license — some fonts explicitly forbid embedding or require a special webfont license. I learned that the hard way and paid for a license afterwards, so consider licensing first. My preferred approach when starting from a DOCX is to convert with Pandoc or export to EPUB and then fix the result in an EPUB editor. With Pandoc you can include fonts directly using --epub-embed-font=path/to/font. For example: pandoc mydoc.docx -o mybook.epub --epub-embed-font=fonts/MyFont.woff2 --epub-stylesheet=styles.css. In styles.css add an @font-face block: @font-face { font-family: 'MyFont'; src: url('fonts/MyFont.woff2') format('woff2'); font-weight: normal; font-style: normal; } Then set body, h1 etc to use 'MyFont'.woff2 and provide fallbacks. If you already have an EPUB, open it in Sigil or Calibre’s EPUB editor, create a fonts/ folder (or add to existing), import the .woff/.woff2/.ttf files, edit your stylesheet to include @font-face, and check that content.opf has items for each font (e.g. ). Most readers prefer woff or woff2, but include ttf/otf only if you must; webfont formats are lighter and more appropriate for EPUB. A few gotchas I always warn friends about: Microsoft Word’s EPUB export often ignores embedded DOCX fonts, so don’t rely on the DOCX embed option as your final step. Kindle devices/apps are inconsistent — Amazon converts uploaded EPUBs and may strip or substitute fonts unless you convert to azw3/EPUB3 properly; test on the target devices (Apple Books and Kobo tend to respect embedded fonts more reliably). Also provide sensible fallbacks in CSS because some older readers will ignore custom fonts. Finally, remember embedding fonts increases EPUB size, so subset fonts where allowed (tools or services can subset), and test extensively. I like the visual control embedded fonts give — there’s nothing like seeing your book look the way you designed it on an iPad — but it’s also a bit of housekeeping work. I enjoy the balance of design and technical fiddling; it keeps publishing interesting.