No. 5 of 42 ·Voicemail Drop Software

Drop Cowboy

Web · API · paid plans from $125/mo

Freedom report

Two barsScore 6.4

Free tierA free tier is on its own pricing page
Open codeNo open-source code on record
Runs widely1 of 6 device platforms
DocumentedPlans, terms and facts published

Drop Cowboy is ranked #5 of 42 in voicemail drop software on Freedom251. It runs on API, Web. There is no free plan. Paid plans start at $125/mo.

Drop Cowboy plans and pricing

All plans

Wholesale BYOC Free + carrier fees Varies by volume · Requires Twilio or compatible SIP provider · Unlimited campaigns dropcowboy.com · 1 Oct 2026

Prime $125/mo 62,762 Messages/Year · Additional messages: 2.1¢ each · Unused funds roll over dropcowboy.com · 1 Oct 2026

Large Business $250/mo 136,986 Messages/Year · Additional messages: 1.9¢ each · Priority support dropcowboy.com · 1 Oct 2026

Extra-Large $500/mo 301,508 Messages/Year · Additional messages: 1.7¢ each · Priority support dropcowboy.com · 1 Oct 2026

Enterprise $1,000/mo 670,391 Messages/Year · Additional messages: 1.5¢ each · Dedicated onboarding dropcowboy.com · 1 Oct 2026

Ultra $4,000/mo 3,221,477 Messages/Year · Additional messages: 1.2¢ each · Dedicated onboarding dropcowboy.com · 1 Oct 2026

Compared on voicemail drop software

Free plan: No
Drop trigger: both
CRM integrations: Yes
Scheduled drops: Yes
Drop analytics: Yes
Contact import: both

Best Drop Cowboy alternatives

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The record

Core product: Drop Cowboy delivers ringless voicemail, SMS, MMS, and voice broadcast messages through one communications platform.
AI voice cloning: Mimic AI can clone a voice from a 30-second sample and insert names, addresses, and other custom fields into messages.
Automation: The platform supports automated workflows, scheduling, merge fields, A/B testing, analytics, and CRM-triggered campaigns.
Integrations: Drop Cowboy lists native connections for Salesforce, HubSpot, Zoho, Pipedrive, Keap, and more than 100 CRMs, plus Zapier and a REST API.
Compliance tools: The service provides DNC scrubbing, suppression lists, consent tracking, and time-zone-aware quiet-hours enforcement for TCPA-related outreach.
Security: Drop Cowboy states that data in transit uses 256-bit SSL/TLS encryption and that stored data is encrypted at rest.
Compliance standards: The security page states adherence to GDPR, CCPA, TCPA/TFR, and regular third-party security audits.
Support: Every customer gets a dedicated account manager, with US-based support, live chat, email, and phone assistance.
Sending limit: Usage-based plans are limited to 120,000 messages per hour per campaign.
Calling limit: Dialer seats include up to 24 hours of talk time per seat per day; excess usage is billed at the messaging plan's per-message rate.
Additional fees: A $0.0031 compliance fee applies per message, while Mimic AI voice cloning is billed at $0.005 per 100 characters.
Target customers: Drop Cowboy says it serves real estate, financial services, healthcare, retail, automotive, solar and home services, government, and other industries.
Founded: 2017
Headquarters: Sheridan, Wyoming, United States
Price from: $125/mo

Where it ranks on Freedom251

Best Voicemail Drop Software in 2026#5 of 42

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Sources

dropcowboy.com/features· checked 1 Oct 2026
dropcowboy.com· checked 1 Oct 2026
dropcowboy.com/features/integrations· checked 1 Oct 2026
dropcowboy.com/about· checked 1 Oct 2026
dropcowboy.com/security· checked 1 Oct 2026
dropcowboy.com/messaging-pricing· checked 1 Oct 2026