Compatibility Checklist: Avoiding Formatting Headaches When Moving Documents from Word to LibreOffice

Stop losing time and format fidelity after an acquisition — a practical checklist to keep acquired companies' Word files usable in LibreOffice

Hook: Mergers and acquisitions are stressful; the last thing your operations team needs is hundreds of legal, HR, and finance documents that break when opened in LibreOffice. In 2026, with more organizations favoring open formats and offline workflows, software compatibility is now an M&A operations risk: lost templates, broken macros, substituted fonts, and corrupted numbering slow post-close integration. This checklist gives you the exact tests, fixes, and acceptance criteria to preserve document fidelity when moving files from Word to LibreOffice.

Why this matters in 2026

Recent trends (late 2024–2026) accelerated migrations away from cloud subscription office suites. Governments and privacy-sensitive enterprises renewed interest in open standards and local-first tooling, and LibreOffice releases in 2024–2025 improved compatibility—but no conversion is flawless. At scale, acquired-company documentation becomes a compliance and productivity bottleneck if you treat file migration as a bulk copy. Treat it instead as an operational project with measurable acceptance criteria.

How to use this checklist

This is a practical, ordered checklist for M&A and operations teams. Use it during due diligence and again during post-close integration. Each item finishes with a simple test and an acceptance criterion so you can sign off on document usability.

Pre-migration audit (essential)

1. Inventory files
   • Count and categorize: contracts, templates (.dotx/.dotm), policies, invoices, forms, spreadsheets with embedded objects.
   • Mark high-value/doc-critical files (legal, vendor contracts, SEC filings) for prioritized manual migration and QA.

   Test: Export a file list (path, extension, size, last-modified) and sample 10 top-value files.

   Acceptance: Inventory CSV exists and top 10 files are flagged with ownership and migration priority.

2. Identify macros & automation
   • Scan for VBA macros, COM/ActiveX controls, add-ins, and external data connections.
   • Flag all .docm/.xlsm files and templates that contain automation.

   Test: Automated scan (PowerShell or grep for "Sub " in .docm/.dotm) and manual review of flagged files.

   Acceptance: Macro inventory with owner and purpose is documented.

3. Check fonts
   • List embedded fonts and fonts used in styles. Note any proprietary fonts or company-branded typefaces.

   Test: Use a script or font inspector to output all font names used across docs.

   Acceptance: Fonts documented and a plan exists for substitution or embedding.

Templates & styles: fix the source, not each doc

Direct formatting is the number-one source of drift. Convert templates, not only individual files.

1. Consolidate templates
   • Collect every .dotx, .dotm and corporate template. Decide which will become LibreOffice .ott templates.
   • Rename and document template purpose and style names (e.g., "Heading 1 – Legal").

   Fix: Open each template in Word, switch all formatting to named styles (Headings, Normal, Caption). Save a clean .docx and then convert to .ott in LibreOffice's Template Manager.

   Test: Create a new document from the converted .ott and verify naming and style behavior.

   Acceptance: 95% of templates open and produce identical heading levels and paragraph spacing in LibreOffice.

2. Style-name mapping
   • Document a mapping table: Word style name -> LibreOffice style name (if different).

   Fix: Where styles differ, create matching styles in LibreOffice templates with exactly the same names and attributes.

   Test: Batch-convert sample docs and compare headings, TOC, and numbering.

3. Numbering and cross-references
   • Complex multi-level lists and cross-references often break. Rebuild numbering in templates rather than relying on local list overrides.

   Fix: Recreate multi-level lists in LibreOffice using styles, then update documents to use those styles.

   Acceptance: All automated numbering and table of contents regenerate correctly with fewer than 2 manual edits per 100 docs.

Macros & automation: rewrite, sandbox, or replace

VBA macros do not fully run inside LibreOffice. Treat macros as a migration project with three options: rewrite, replace with server automation, or deprecate.

1. Inventory and classify macros
   • Classify by complexity: simple (formatting, find/replace), medium (data import/export), complex (COM + ActiveX, Office-only APIs).

   Test: Run macros in a controlled environment and capture inputs/outputs for each.

2. Choose a migration strategy
   • Rewrite to LibreOffice Basic when logic is simple and interacts only with document text.
   • Re-implement as a small Python script or microservice using the UNO API for cross-platform automation and headless conversion.
   • Replace with a SaaS workflow (document generation tools or RPA) where appropriate—common in 2026 as more vendors provide secure, private automation options.

   Fix: For each macro, pick the strategy and create a ticket with estimated effort.

   Acceptance: All business-critical macros are either re-implemented or have a validated manual process and documented SLA.

3. Security-first approach
   • Treat macros as malware risk. Scan with current AV and run in isolated VMs before conversion.

   Test: Ensure sandboxed execution and verify no external network calls unless explicitly allowed.

Fonts: preserve brand and layout

Fonts cause visual drift, line breaks, and pagination differences. Plan proactively.

1. Prefer open, embeddable fonts
   • Where possible, replace proprietary corporate fonts with equivalent open fonts (Google Fonts family equivalents) before conversion.

   Fix: Update templates and styles to use chosen fonts. Keep a company font pack deployed to user devices or centrally installed in your Windows/Linux image.

2. Embed or bundle fonts
   • Word allows embedding fonts into .docx; LibreOffice respects some embedded fonts but may not reliably embed them into ODF. For critical docs, export a PDF fallback.

   Test: Convert important documents and compare PDFs generated by Word and LibreOffice; confirm no reflow or glyph substitution.

3. Font substitution map
   • Set a substitution table in LibreOffice (Tools > Options > Fonts) for enterprise-deployed LibreOffice installations.

   Acceptance: Key brand documents show identical line breaks and pagination in both environments or have approved fallbacks.

Images, SmartArt, and embedded objects

Vector art, SmartArt, and embedded charts frequently lose editability. Decide what's required post-migration.

• SmartArt/SmartShapes: Convert to high-resolution images or rebuild as native LibreOffice Draw objects for editable assets.
• Embedded Excel charts: Extract the source data and re-link charts in LibreOffice Calc where necessary.
• Equations: Office Math (OMML) may not port cleanly; convert to MathML or images when editing is not required.

Test: Open documents and check chart rendering, image quality, and whether edits are possible where needed.

Forms, fields, and signatures

Interactive forms and digital signatures are mission-critical for legal and HR docs.

• Legacy Word form fields: Replace with LibreOffice form controls or convert to fillable PDF if signatures are required.
• Digital signatures: Verify that existing digital signatures remain valid after conversion; they often don't, so capture signed copies as final PDFs.
• Field codes: Update TOC and cross-reference fields by refreshing them in LibreOffice (Tools > Update > Fields).

Metadata, compliance, and auditing

Hidden metadata can be a compliance hazard during M&A. Use document inspection and redaction tools.

• Run document inspectors in both Word and LibreOffice to strip comments, tracked changes, and hidden properties before external sharing.
• Keep an audit log of conversion actions (who, what, when) for the acquisition compliance records.

Automated conversion & QA workflows

At scale, manual conversion is impossible. Use headless conversions and automated comparisons.

• Use headless LibreOffice: soffice --headless --convert-to odt filename.docx
• Use unoconv or UNO-based Python scripts for batch processing and pre/post scripts to fix known issues.
• Automated visual diff: Convert both original and converted files to PDF (Word and LibreOffice) and run a PDF visual-diff to detect layout changes.
• Unit test templates: For each template, define sample content and an automated verification routine that checks styles, TOC, numbering, and page counts.

Acceptance criteria and SLA examples

Turn each checklist item into measurable acceptance criteria and SLAs for the post-close integration team.

• Template fidelity: less than 2 visual differences per 100 pages in sample tests.
• Macro functionality: 100% of business-critical macros re-implemented or valid manual process documented within 30 days.
• Fonts: critical brand documents match exactly; others within an acceptable substitution threshold (1–3 glyph changes).
• Forms & signatures: signed documents archived as PDFs; new forms converted to fillable ODF/PDF with user acceptance testing.

Case study (experience): Holding-co migration — 2025

We worked with a mid-market holding company in late 2025 that acquired three SMBs with mixed Word and Google Docs files. Problems found: 120 templates with inconsistent style names, 60 macro-enabled templates, and two proprietary fonts. Outcome after applying this checklist:

• Templates consolidated to 12 corporate .ott templates with unified style names.
• 30 macros rewritten as small Python services using the UNO API; non-critical macros were deprecated.
• Proprietary fonts replaced with visually equivalent open fonts after brand approval; legal documents were preserved as signed PDFs.
• Result: post-close admin time reduced by 40% and zero contract disputes from formatting errors within 90 days.

Advanced strategies and 2026 trends

Use these forward-looking tactics to reduce future conversion costs and leverage new tools:

• Local LLM-assisted mapping: In 2026, privacy-first LLMs are used internally to map styles and suggest macro rewrites. Use local models to avoid sending sensitive documents to cloud AI.
• Standardize on ODF-first templates: The fastest way to reduce future work is to maintain canonical templates in ODF and export to Word only for external partners.
• Continuous integration for documents: Treat templates and automation as code. Use git, CI pipelines, and automated rendering tests to catch regressions when templates change.
• Hybrid workflows: Adopt a dual-system approach where editing and heavy automation remains in Word for narrow use-cases while general operations use LibreOffice.

Tooling checklist (practical)

• Headless LibreOffice (soffice) for batch conversion
• unoconv or Python UNO scripts for automation
• PDF visual-diff tools (commercial or open-source)
• Font inventory scripts (fc-list on Linux or PowerShell on Windows)
• Document scanner for macros (basic scripts to grep for "Sub ", "AutoOpen", "Declare")
• Sandbox VMs for macro testing

Quick migration checklist (one-page summary)

1. Inventory files and flag critical docs.
2. Extract and document templates; create canonical style map.
3. Identify and classify macros; choose rewrite/replace/deprecate.
4. Create font strategy (replace/embed/substitute).
5. Batch-convert templates to .ott and test new docs from template.
6. Automate bulk conversion with headless LibreOffice + visual diffs.
7. Archive signed originals as PDFs; confirm signatures where needed.
8. Document acceptance criteria and track remediation tickets.

Pro tip: Prioritize templates and macros used in revenue- or compliance-critical processes. Converting non-essential marketing or internal docs can be deferred.

Checklist ownership and timelines

Assign a small cross-functional team: IT (conversion tooling), Legal (contracts & signatures), HR (forms), and Operations (templates & acceptance). Example timeline for a 1,000-document portfolio:

• Week 0–1: Inventory & classification
• Week 2–4: Template consolidation and priority conversions
• Week 4–8: Macro migration and automation builds
• Week 8–12: Full batch conversion, QA, and sign-off

Closing: operationalize the checklist

Moving files from Word to LibreOffice during an acquisition isn't a one-off IT task — it's an operational project with compliance, security, and user-adoption implications. Use this checklist to convert templates first, treat macros as discrete projects, and enforce measurable acceptance criteria. In 2026, the most resilient organizations will adopt ODF-first governance, local AI tools for mapping, and CI-style testing for documents.

Actionable takeaways:

• Always convert and fix templates before migrating content documents.
• Classify and triage macros — don’t assume VBA will work.
• Standardize fonts and test PDFs to prevent layout drift.
• Automate batch conversion and visual QA, and keep an audit trail for compliance.

Next steps (call-to-action)

Ready to protect your post-acquisition operations? Download our ready-to-run migration checklist and sample scripts, or book a migration review with our GPL-compliant conversion specialists to build a migration plan tailored to your portfolio. Ensure your acquired company’s documents stay usable, secure, and compliant — without slowing down day-one operations.

Related Reading

• From LEGO to MTG: Creating Fan-Focused Bonus Campaigns That Appeal to Gamers and Collectors
• Set the Ramadan Ambience: Using Affordable Smart Lamps (Govee) for Iftar & Quran Time
• Build a High-Density, Cost-Optimized Seedbox: Selecting Drives as PLC NAND Arrives
• Integrating Live Tow Dispatch Into Real Estate Platforms and Membership Portals
• Top Photo Angles & Golden-Hour Times for The Points Guy’s 2026 '17 Places' List