Skip to main content
    Back to Industry Insights
    Procurement
    Business Practices
    Compliance
    Legal

    12 Questions to Ask Before an Enterprise Software Renewal in 2026

    Preparing for a major enterprise software renewal? Use this 12-question checklist to pressure-test contract terms, usage data, compliance exposure, and negotiation leverage before signing.

    Hollie Palmer

    Hollie Palmer

    Director of Marketing, LicenseFortress

    May 2026
    14 min read
    12 Questions to Ask Before an Enterprise Software Renewal in 2026

    Preparing for a major enterprise software renewal? Use this 12-question checklist to pressure-test contract terms, usage data, compliance exposure, and negotiation leverage before signing.

    The bottom line

    Preparing for a major enterprise software renewal? Use this 12-question checklist to pressure-test contract terms, usage data, compliance exposure, and negotiation leverage before signing.

    • LicenseFortress is an independent software licensing advocate — we never sell vendor licenses and take no vendor commissions.
    • $2.4B+ in vendor claims defended and $625M+ saved for clients.
    • Coverage across Oracle, Microsoft, IBM, SAP, VMware by Broadcom, and Adobe.
    • Licensing experts working alongside software contract attorneys.

    From our case files

    What asking the right questions before signing was worth:

    Expert Contract Negotiations Transform an Outdated Oracle Agreement

    Packaging company saved $2.5M over 5 years by renegotiating a 20-year-old Oracle contract—6,150% ROI on a $40K engagement.

    Read the case study

    Energy Provider Saves Over $1M After Microsoft True-Up Error Found

    LicenseFortress uncovered a costly Microsoft True-Up error, saving a major energy company over $1 million by identifying overlooked entitlements.

    Read the case study
    Browse all client results

    About the author

    Hollie Palmer

    Hollie Palmer

    Director of Marketing, LicenseFortress

    Hollie translates the LicenseFortress team's licensing expertise into practical guides and checklists.

    Related Articles

    The EU Just Changed SAP Support: What Customers Should Know—and Why the Decision Matters Beyond SAP
    Compliance
    Legal

    The EU Just Changed SAP Support: What Customers Should Know—and Why the Decision Matters Beyond SAP

    August 202611 min read
    Enterprise Software Renewal Strategy: How to Negotiate Better Contracts in 2026
    Procurement
    Business Practices

    Enterprise Software Renewal Strategy: How to Negotiate Better Contracts in 2026

    May 202613 min read
    9 Ways to Find and Remove Unused Software Licenses
    ITAM
    Compliance

    9 Ways to Find and Remove Unused Software Licenses

    June 202613 min read