DiscoverThe Cloud Pod324: Clippy’s Revenge: The AI Assistant That Actually Works - Sort Of
324: Clippy’s Revenge: The AI Assistant That Actually Works - Sort Of

324: Clippy’s Revenge: The AI Assistant That Actually Works - Sort Of

Update: 2025-10-09
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Welcome to episode 324 of The Cloud Pod, where the forecast is always cloudy! Justin, Ryan, and Jonathan are your hosts, bringing you all the latest news and announcements in Cloud and AI. This week we have some exec changes over at Oracle, a LOT of announcements about Sonnet 4.5, and even some marketplace updates over at Azure! Let’s get started. 


Titles we almost went with this week



  • Oracle’s Executive Shuffle: Promoting from Within While Chasing from Behind

  • Copilot Takes the Wheel on Your Legacy Code Highway

  • Queue Up for GPUs: Google’s Take-a-Number Approach to AI Computing

  • License to Bill: Google’s 400% Markup Grievance

  • Autopilot Engages: GKE Goes Full Self-Driving Mode

  • SQL Server Finally Gets a Lake House Instead of a Server Room

  • Microsoft Gives Office Apps Their Own AI Interns

  • Claude and Present Danger: The AI That Codes for 30 Hours Straight

  • The Claude Father Part 4.5: An Offer Your Code Can’t Refuse

  • CUD You Believe It? Google Makes Discounts Actually Flexible

  • ECS Goes Full IPv6: No IPv4s Given

  • Breaking News: AWS Finally Lets You Hit the Emergency Stop Button

  • One Marketplace to Rule Them All

  • BigQuery Gets a Crystal Ball and a Chatty Friend

  • Azure’s September to Remember: When Certificates and Allocators Attack

  • Shall I Compare Thee to a Sonnet? 4.5 Ways Anthropic Just Leveled Up

  • AWS provides a big red button


Follow Up 


01:26 The global harms of restrictive cloud licensing, one year later | Google Cloud Blog



  • Google Cloud filed a formal complaint with the European Commission one year ago about Microsoft’s anti-competitive cloud licensing practices, specifically the 400% price markup Microsoft imposes on customers who move Windows Server workloads to non-Azure clouds.

  • The UK Competition and Markets Authority found that restrictive licensing costs UK cloud customers £500 million annually due to lack of competition, while US government agencies overspend by $750 million yearly because of Microsoft’s licensing tactics.

  • Microsoft recently disclosed that forcing software customers to use Azure is one of three pillars driving its growth and is implementing new licensing changes preventing managed service providers from hosting certain workloads on Azure competitors.

  • Multiple regulators globally including South Africa and the US FTC are now investigating Microsoft’s cloud licensing practices, with the CMA finding that Azure has gained customers at 2-3x the rate of competitors since implementing restrictive terms.

  • A European Centre for International Political Economy study suggests ending restrictive licensing could unlock €1.2 trillion in additional EU GDP by 2030 and generate €450 billion annually in fiscal savings and productivity gains.


03:32 Jonathan – “I’d feel happier about these complaints Google were making if they actually reciprocated the deals they make for their customers in the EU in the US.” 


AI is Going Great – Or How ML Makes Money 


05:14 Vibe working: Introducing Agent Mode and Office Agent in Microsoft 365 Copilot | Microsoft 365 Blog



  • Microsoft introduces Agent Mode for Office apps and Office Agent in Copilot chat, leveraging OpenAI’s latest reasoning models and Anthropic models to enable multi-step, iterative AI workflows for document creation. 

  • This represents a shift from single-prompt AI assistance to conversational, agentic productivity where AI can evaluate results, fix issues, and iterate until outcomes are verified.

  • Agent Mode in Excel democratizes expert-level spreadsheet capabilities by enabling AI to “speak Excel” natively, handling complex formulas, data visualizations, and financial analysis tasks. 

  • The system achieved notable performance on SpreadsheetBench benchmarks, and can execute prompts like creating financial reports, loan calculators, and budget trackers with full validation steps.

  • Agent Mode in Word transforms document creation into an interactive dialogue where Copilot drafts content, suggests refinements, and asks clarifying questions while maintaining Word’s native formatting. This enables faster iteration on complex documents like monthly reports and project updates through conversational prompts rather than manual editing. (FYI, this is a good way to get AI Slop, so buyer beware.)

  • The thing we’re the most excited about, however, is Office Agent in Copilot chat, which creates complete PowerPoint presentations and Word documents through a three-step process: clarifying intent, conducting web-based research with reasoning capabilities, and producing quality-checked content using code generation. (Justin, being an exec, really just likes the pretty slides.) 

  • This addresses previous AI limitations in creating well-structured presentations by showing chain of thought and providing live previews.

  • The features are rolling out through Microsoft’s Frontier program for Microsoft 365 Copilot licensed customers and Personal/Family subscribers, with Excel and Word Agent Mode available on web (desktop coming soon) and Office Agent currently US-only in English. 

  • This positions Microsoft to compete directly with other AI productivity tools while leveraging their existing Office ecosystem.


17:27 Justin – “There’s web apps for all of them. They’re not as good as Google web apps, but they pretend to be.” 


08:14 Introducing Claude Sonnet 4.5 \ Anthropic



  • Claude Sonnet 4.5 achieves 77.2% on SWE-bench verified, positioning it as the leading coding model with the ability to maintain focus for over 30 hours on complex multi-step tasks. 

  • The model is available via API at $3/$15 per million tokens, matching the previous Sonnet 4 pricing.

  • The Claude Agent SDK provides developers with the same infrastructure that powers Claude Code, enabling creation of custom AI agents for various tasks beyond coding. 

  • This includes memory management for long-running tasks, permission systems, and subagent coordination capabilities.

  • Computer use capabilities improved significantly with 61.4% on OSWorld benchmark (up from 42.2% four months ago), enabling direct browser navigation, spreadsheet manipulation, and task completion. 

  • The Claude for Chrome extension brings these capabilities to Max subscribers.

  • New product features include checkpoints in Claude Code for progress saving and rollback, a native VS Code extension, context editing with memory tools in the API, and direct code execution with file creation (spreadsheets, slides, documents) in Claude apps.

  • Early customer results show 44% reduction in vulnerability intake time for security agents, 18% improvement in planning performance for Devin, and zero error rate on internal code editing benchmarks (down from 9%). 

  • The model operates under ASL-3 safety protections with improved alignment metrics.


12:02 Ryan – “I’ve been using Sonnet 4 pretty much exclusively for coding, just because the results I’ve been getting on everything else is really hit or miss. But I definitely won’t let it go off, because it WILL go off on some tangents.” 


16:22 <a href="https://www.databricks.com/blog/claude-sonnet-45-h

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324: Clippy’s Revenge: The AI Assistant That Actually Works - Sort Of

324: Clippy’s Revenge: The AI Assistant That Actually Works - Sort Of

Justin Brodley, Jonathan Baker, Ryan Lucas and Matt Kohn