IT AI Index
Index Vendors › Tailscale · September 2026 Edition
1 category · Ranked

Tailscale

77Judge labels
2First choices
6Negative labels
12 of 12Models named it
1Category
September 2026 Edition. Every number here is derived from the raw labels under vendor table vv2026-09.2, every buyer segment counted.
Best standing
4% in ZTNA for small business buyers
Rank 11 of 71 in the mid-market standingaccepted challenger
0 of 12 models made it the first choice on the direct prompt; 11% of its 19 labels there were negative.
By buyer segmentRead the same way at every buyer size.
In ztna · each standing computed within its segment · bars are 0 to 100 · the accent bar is the product's own best reading

Standing by category

Every category where a model named Tailscale for a mid-market B2B company. Share is first choices across the direct, paraphrase, budget and scale prompts; rank is within every product named in that category.
CategoryFunctionShareRankNegative rateLabelsQuadrant
Zero trust network accessNetwork and edge0%11 of 7111%19accepted challenger

Movement

This is the first edition on this tier, so no move can be computed for Tailscale yet. From the next edition this section shows, per buyer segment, whether its share moved by more than the measured noise floor.

By model

How each model treated Tailscale across every prompt where it was named for a mid-market B2B company. Twelve models, six prompts per category.
ModelFirst choiceAlternativeMentionNegativeLabels
Claude Haiku 4.502002
GPT-5.4 mini00000
Gemini 3.5 Flash03003
Perplexity Sonar00000
Grok 4.1 Fast02103
Mistral Small01001
DeepSeek V4 Flash03014
Llama 4 Maverick00000
Qwen 3.7 Flash02013
Kimi K201001
GLM 4.7 FlashX01001
MiniMax M2.500101

By framing

Which of the six questions produced the naming. By model says how often; this says asked what. The first-choice count on the right carries the marks of the models that produced it.
FramingLabels by classFirst choices
Direct7 labelsNone
Paraphrase15 labels1
Comparative20 labels6not counted in share
Budget-constrained17 labels1
Scale-constrained8 labelsNone
Negative10 labels1not counted in share
First choiceAlternativeMentionNegative77 labels in all, every segment counted; 2 of the 9 first choices count toward share, since the comparative and negative framings do not. The bar is one segment per label class, to scale within the framing.

What the models said for it

Verbatim evidence the judge attached to positive labels.

“For startups under 10 users, Tailscale (free for 3) or Twingate (free for 5) layered on identity you already own costs nothing to start.” Claude Haiku 4.5 · ZTNA · budget prompt · alternative
“software-first ZTNA solutions (e.g., Twingate, Tailscale). They are exceptionally fast to deploy and maintain” Gemini 3.5 Flash · ZTNA · scale prompt · alternative
“Excellent for dev-heavy B2B or mesh networking... but more network-oriented than app-specific ZTNA” Grok 4.1 Fast · ZTNA · paraphrase prompt · alternative
“Provides a free tier for up to 3 users, making it a good choice for very small teams or startups” Mistral Small · ZTNA · budget prompt · alternative

And against it

Verbatim evidence attached to negative labels. A warning on a product with few labels is a warning; on a product with many, it is one voice among them.

“Verdict: Avoid Tailscale for critical production infrastructure until their Workload Identity Federation (WIF) rollout is fully matured” Qwen 3.7 Flash · ZTNA · negative prompt · hard negative
“The hosted coordination server is a single point of trust” DeepSeek V4 Flash · ZTNA · negative prompt · soft negative

Named alongside

The products named in the same answers as Tailscale, over the 77 answers that named it. Took the first choice instead counts the answers where the other product was the first choice and Tailscale was named but was not.
ProductSame answerTook the first choice insteadHead to head
Twingate60 of 7723Not in the top three
Cloudflare One50 of 7733Not in the top three
Check Point Harmony SASE36 of 770Not in the top three
Zscaler Private Access26 of 777Not in the top three
Palo Alto Networks Prisma Access17 of 771Not in the top three
Zscaler15 of 771Not in the top three
OpenVPN CloudConnexa14 of 773Not in the top three
NordLayer12 of 770Not in the top three
Cloudflare Access11 of 772Not in the top three
Netskope11 of 771Not in the top three
A head-to-head page exists where both products are in a category's top three. The other rows are the same fact without a page behind them, so they link to the product instead.

What carried it into the answer

The sites and pages cited by the answers that named Tailscale. A fact about retrieval, not a lever on the model.

Citations exist only for the models that return a source list, four of the twelve in this edition, so these counts come from 59 of the 77 answers that named Tailscale and are not a share of its labels.

Domains cited

cybersecuritynews.com44
petronellatech.com42
cyberpress.org30
startwithidentity.com28
aimultiple.com24
portnox.com20
costbench.com17
eastbaycyber.com16
itbusinessedge.com16
meshwg.com16

253 of the 253 domain citations in answers naming Tailscale came from somebody else's page.

Pages cited

Pages are listed as the models cited them.

Is this your product?

Claim this page

Claiming is free and changes nothing in the data. A claimed page shows a verified contact who is told when each edition publishes and when Tailscale's standing changes by more than the noise floor; the right to propose corrections to the vendor table, meaning names the judge wrote that should or should not read as Tailscale, applied by version and listed in the change log; and a one-line description supplied by the vendor and marked as such.

It does not get any change to labels, shares or verdicts, any preview, or any say over which quotes appear. A verification link goes to your work email; an address at tailscale.com is approved on the spot, any other address is reviewed by hand.

Your name and company appear on the claimed page, or the company alone if you ask below. A title and a LinkedIn address appear there too if you give them, and are left off if you do not. Your email address is never published.

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