Enterprise Search Is Back, Baby, or Is It Spelled Baiby
October 28, 2025
This essay is the work of a dumb dinobaby. No smart software required.
I want to be objective, but I admit I laughed. The spark for my jocularity was the marketing content document called “Claude AI Integrates with Microsoft 365 and Launches Enterprise Search for Business Teams.” But the subtitle tickled by aged ribs:
Anthropic has rolled out two new enterprise features for Claude, integration with Microsoft 365 and a unified search tool designed to connect organizational data across platforms.
There is one phrase to which I shall return, but let’s look at what the document presents as actual factual, ready to roll, enterprise ready software plus assorted AI magic dust.
Thanks, Venice.ai. Good enough.
I noted this statement about Microsoft / Anthropic or maybe Anthropic / Microsoft:
“Introducing two new features: Claude now connects to Microsoft 365 and offers enterprise search,” the company wrote on LinkedIn. “You can connect Claude to SharePoint, OneDrive, Outlook and Teams to search documents, analyze email threads, and review meeting summaries directly in conversation.” Anthropic, known for developing AI models focused on reliability and alignment, said both features are available immediately for Claude Team and Enterprise customers.
The Holy Grail is herewith ready for licensees to use to guzzle knowledge.
But what if the organization’s information is partitioned; for example, the legal department has confidential documents or is engaged in litigation and discovery is underway? What if the organization is in the pharmaceutical business, and the work is secret with a bit of medical trials activity underway. There are interview notes, laboratory data, and photographs of results? What if the organization lands a government contract with the Department of War and has to split off staff quickly as they transition from “regular” work to that which is conducted under quite specific rules and requirements? There are other questions as well; for example, what about those digitized schematics, the vendor information, and the data from digital cameras and work monitoring software?
I noted this statement as well:
Anthropic said the capability “brings your company’s knowledge into one place, using a dedicated shared project.” The system also includes custom prompts to refine searches and improve response accuracy. The company emphasized use cases such as onboarding new team members, identifying experts across departments, and analyzing feedback patterns to guide strategy and decision-making. The Microsoft 365 connector and enterprise search are now live for all Claude Team and Enterprise customers. Organization administrators can enable access and configure connected data sources.
My reaction, “This is 1990s enterprise search wearing a sweatshirt with a robot and AI on the front.”
Is this possible? Sure. The difficulty is that when employees interact with this type of system, interesting actions take place. One of the most common is, “This is not the document I wanted.” Often an employee will say, “This is not the PowerPoint I signed off for use at the conference.” Others may say, “Did you know that those salary schedules are in an Excel file with the documents about the employee picnic?”
Now let’s look at the phrase I thought interesting enough to discuss it in a separate paragraph. Here’s the phrase: “organizational data across platforms.” This evokes the idea that somewhere in the company is a cloud service containing corporate data. The Anthropic or Microsoft system will spider that content, process it, and make it findable. The hitch in the git along is that the other platforms may not embrace Microsoft security methods. Further the data may require a specific application to access those data. The cycle time between original indexing of the other platforms may be out of sync with the most recent data on those other platforms. In a magic world like the Fast Search & Transfer type environment which Microsoft purchased in 2008, the real world caused the magic carpet to lose altitude.
Now we have magic carpet 2025. How well with the painful realities of resources, security, cost, optimization, and infrastructure make it difficult for the magic carpet to keep flying? Marketing collateral pitches are easy. Delivering AI-enabled search to live up to the magic is slightly more difficult and, in my experience, shockingly expensive.
Stephen E Arnold, October 28, 2025
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