Oracle made a $300B bet on OpenAI. It's paying the price

Enterprise dissatisfaction and migrations

  • Many commenters report strong negative sentiment toward Oracle in their organizations, often citing “predatory” behavior, aggressive audits, and licensing/Java subscription tactics.
  • Several enterprises are actively trying to reduce or eliminate Oracle, typically by:
    • Building institutional experience with PostgreSQL or other DBs at the departmental level first.
    • Migrating low‑risk or “low‑hanging fruit” workloads, then gradually larger systems.
    • Using AWS RDS or similar to add an abstraction layer and weaken the direct Oracle relationship.
  • Some vendors are dropping Oracle support and providing migration paths (often to SQL Server), reinforcing the “trend away.”
  • One anecdote describes a large bank slowly decoupling from Oracle middleware/DBs as part of a broader modernization and Sun hardware retirement.

Difficulty, risk, and economics of switching

  • Multiple replies stress that moving off Oracle is extremely hard, expensive, and politically risky, often taking many years and risking failed or partial migrations.
  • Even if Oracle is expensive, the migration cost and risk (including potential outages and dual‑system operation) can dwarf annual savings.
  • Others argue that in some cases the cost savings are so large (e.g., many millions per year) that the risk is justified, though these are framed as exceptions requiring long, staged efforts.

Contract structure and renewal dynamics

  • Discussion around 10‑year “unlimited” enterprise agreements:
    • Not typical for most software, but plausible for very large infrastructure deals.
    • These can feel cheap upfront but lead to painful “true‑ups” later as usage grows.
    • Some enterprises have used the 10‑year window to move workloads off Oracle before renewal to gain leverage.
  • Skeptics question how widespread such contracts are and request sources; others note that Oracle has weathered similar “we’re moving off” talk for decades.

Oracle vs. competitors (SAP, PostgreSQL, SQL Server)

  • One story: after an RFP process, a company chose SAP over Oracle due to concerns about Oracle’s honesty and behavior, despite SAP’s own issues; HANA itself then created technical and cost problems.
  • Some technical managers still reflexively view Oracle as the only “real” enterprise DB and distrust PostgreSQL, especially where commercial Postgres support is weak.
  • Others argue almost no one picking a greenfield system today chooses Oracle DB unless pulled in via an Oracle/SaaS application.

Java, Oracle, and developer sentiment

  • Strong disagreement on whether Oracle “destroyed” or “rescued” Java:
    • Some say post‑acquisition years were worrying but Java is now in its best technical shape (JDK pace, performance, tooling).
    • Others claim Oracle’s licensing and lawsuits eroded goodwill, and that few new developers choose Java voluntarily, even though it remains ubiquitous in big enterprises.
  • Several note that large-scale high-performance systems (e.g., Netflix-like workloads) still lean heavily on Java/HotSpot; newer languages may have more “hype” than actual deployment share.

AI/OpenAI bet and market risk

  • Some commenters say headlines misstate the situation, arguing Oracle is being paid huge sums by OpenAI rather than “betting” $300B on it.
  • Others point to credit default swap pricing and debt market signals indicating Oracle’s AI-related capex and contracts are seen as risky, though not catastrophically so.
  • One view: even if many AI projects fail, Oracle’s “support and lock‑in” model might profit from enterprises deploying fragile AI systems that need intensive care.

Why Oracle persists

  • Reasons given for continued Oracle use:
    • Legacy decisions with deep lock‑in (proprietary extensions, decades of apps built around Oracle).
    • Enterprise features, certifications, compliance, and “one throat to choke” support.
    • Government and large corporate procurement habits; Oracle often bundled with major ERP/financial packages.
  • Some users praise Oracle Cloud’s pricing and footprint (while still avoiding Oracle DB itself on that cloud).