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VERDICT

Should I use Tails (Trytails)?

Best dog care in Chicago, matched to your dog - trytails.com

Depends. Buy if you're a Chicago dog owner who wants matched, vetted walkers plus a genuinely free GPS and poop tracker. Skip it if you're outside Chicago or want the sitter scale of Rover or Wag.

Confidence

Medium. Based on 20+ public sources; most product claims come from Tails' own channels — independent user reviews are scarce.

Ratings

  • Value for money
  • Ease of use
  • Feature depth
  • Support quality
  • Security posture

Pricing

Free

GPS & health tracking app

ModelNot disclosed
Monthly feesNot disclosed
HardwareNot disclosed
Free tierYes
Walks & pet sittingSee pricing page

Best for

  • Chicago dog owners wanting matched, vetted walkers
  • Pet parents who want free GPS and poop tracking
  • Owners who vet walkers on handling, not just stars
  • Reactive-dog owners walking crowded city neighborhoods

Not for

  • Dog owners outside Chicago — matching is neighborhood-local
  • Multi-sitter businesses needing Time To Pet-style scheduling software
  • Anyone wanting the biggest national sitter marketplace
  • Rural or suburban owners needing on-demand city-style coverage

Gotchas - check before you buy

medium

Yelp shows quote-based pricing; confirm final fees before booking

medium

Guess: free GPS tracker doubles as lead-gen; expect upsell to paid bookings

low

Name collides with Supertails and other pet brands; verify you're booking Tails Co.

low

Neighborhood coverage varies; check your area before committing

Pros and cons

Pros

  • Free GPS dog tracking and poop tracker on iOS and Android
  • Matches walkers to your dog; reviews cover handling quality
  • Founder personally answers pet-care questions in community groups
  • Bootstrapped — no private equity or venture investors
  • Publishes trust-and-safety details, including home access handling

Cons

  • Chicago-focused coverage; little evidence beyond the city
  • 358 Instagram followers suggests a very small user base
  • Solo-founder operation; product promoted via build-in-public threads
  • Competes against Rover and Wag with a far smaller network

Sources & method

Analyzed 9/30/2026 - 11 sources - No known vulnerabilities found in the sources reviewed.

official x5review x4security x2

Key stats

  • Value for money: 4/5

    Rating

  • Free

    Starting price

  • 11

    Sources

  • Analyzed

  • Value for money: 4/5. Free tracker tier; publishes pricing page openly
  • Ease of use: 3/5. Consumer app; no usability complaints or praise found
  • Feature depth: 4/5. Matching, GPS, poop tracking, gamified leaderboards
  • Support quality: 4/5. Founder answers questions personally in Facebook groups
  • Security posture: 3/5. Trust and security pages published; no incidents found
  • Yes Free GPS tracking app Walk + poop tracker on iOS and Android
  • iOS + Android Platforms Both app stores listed
  • 358 Instagram following Small for a pet brand
  • Chicago, IL Headquarters 680 N Lake Shore Dr

Pricing

GPS & health tracking app

Free

  • Walk and poop tracking
  • Leaderboard gamification
  • iOS and Android

Walks & pet sitting

See pricing page

  • Per-walk rates not published in reviewed sources
  • Quote available via Yelp listing

Security

No known vulnerabilities found in the sources reviewed.

What users say

Independent user reviews are scarce; most visible posts and praise come from the founder and the company's own channels.

Full analysis

Based on 20+ public sources; most product claims come from Tails' own channels — independent user reviews are scarce.

Solid for Chicago dog owners wanting matched walkers + free GPS tracking; Rover/Wag win on nationwide coverage.

Methodology

Based on 20+ public sources; most product claims come from Tails' own channels — independent user reviews are scarce.

Sources

  1. Tails: Best Dog Care in Chicago | Matched to Your Dogtrytails.com
    official
  2. Pricing & Services | Tailstrytails.com
    official
  3. Best Dog Walking Apps 2026: Rover vs Wag vs Tailstrytails.com
    official
  4. Trust and Safety: 2026 Costs & Ratestrytails.com
    security
  5. Privacy Policy | Tailstrytails.com
    security
  6. TAILS, CO. — Yelpyelp.com
    review
  7. Tails: Dog Walking & Pet Care App — App Storeapps.apple.com
    review
  8. Tails: Dog Walk & Poop Tracker — Google Playplay.google.com
    review
  9. Tails on Instagraminstagram.com
    official
  10. Founder build-in-public postreddit.com
    official
  11. Founder answering pet-care questionsfacebook.com
    review

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