Tailscale, the Toronto startup that sells virtual private network software to companies, is updating its products to help simplify how businesses manage and track their AI use.
The company announced on Tuesday that it is adding new capabilities to Aperture as it looks to help clients contend with the ever-shifting AI market. They include: a chat geared towards reducing shadow AI use; connectors designed to help AI tools access corporate data while preserving user and agent identity; and controlled environments for AI agents to work in.
“The best model, interface, sandbox, and data connection will keep changing. Companies should not have to rebuild their AI setup every time one of those pieces changes.”
AI use is flooding through organizations, and it can be tough to track. Moreover, some vendors are pushing closed AI stacks, despite the fact that the top available AI models and tools are frequently being replaced. Tailscale co-founder and CEO Avery Pennarun is skeptical that this state of play will stabilize “any time soon.”
“The best model, interface, sandbox, and data connection will keep changing,” Pennarun argued in a news release. “Companies should not have to rebuild their AI setup every time one of those pieces changes.”
Tailscale aims to help customers avoid such lock-in and manage AI use practically with Aperture, its AI access and control platform. The startup is building the platform, which is currently available in beta, into “a stable layer for identity, access, and control, so [corporate clients] can keep changing tools without losing track of who is doing what,” Pennarun said.
“Adding the chat-based interface turns Aperture from an engineering tool into a business tool,” Pennarun told BetaKit over email. “To date, Aperture has had success with teams using coding agents … Now, a much wider range of employees can run all of their AI queries and workloads through Aperture.”
The US government’s recent decision to suspend all access to Anthropic’s latest Mythos and Fable models for foreign nationals—including those employed by the AI company—has thrust control over AI into the spotlight and made even more apparent the need for businesses to refrain from relying too heavily on certain providers.
“That situation is a useful reminder that model access can change for reasons completely outside a company’s control,” said Pennarun. “For Canadian companies, that matters. If your AI workflows are hardwired to one provider, one policy change, pricing change, availability issue, or access restriction can become an operational problem.”
With Aperture, Tailscale aims to help companies keep their AI stacks “modular.” Today’s announcement marks the latest step in Tailscale’s push beyond just building an easier VPN to giving clients fast, private access to the applications, devices, infrastructure, and AI systems they need.
RELATED: Tailscale makes first acquisition with Border0 purchase
Tailscale, which was featured in BetaKit Most Ambitious, closed $230 million CAD in Series C funding last year on the back of strong demand from AI companies. Today, it serves more than 30,000 businesses globally, including Cohere, Duolingo, Instacart, Lovable, Microsoft, Mistral, Nvidia, SAP, and Telus.
Pennarun sat down with BetaKit in 2025 to unpack how pressure to adopt AI has created a “Wild West” for corporate cybersecurity, and lay out his startup’s plan to become the air traffic control system for AI—a target that Toronto cybersecurity firm 1Password is also working towards in its own way. For its part, Tailscale made its first acquisition earlier this year to support that vision, buying Vancouver’s Border0.
Feature image courtesy Web Summit Vancouver. Photo by Florencia Tan Jun via Sportsfile.
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