Comparison

Bennie vs WhenFree

Price, ratings, monetisation and update history for both apps, side by side — with what reviewers say about each.

Head to head
About

Bennie

This app helps you understand and manage your employee benefits on the go. View your current benefits, find in-network providers, and access support for any benefit-related questions. It also offers a marketplace for supplementary services.

Highlights
  • View current benefits
  • Access ID cards
  • Find in-network providers
  • Ask benefit-related questions
  • Request appointments
  • Marketplace for supplementary services
Features
Read full description

Bennie is your go-to benefits app to help you and your family understand and manage your benefits wherever you are! BENEFITS • View your current benefits • See balances and access ID cards FIND PROVIDERS • Browse for in-network doctors ASK BENNIE • About anything related to your benefits • Request appointments • Get support MARKETPLACE Supplement your company's benefits with free or discounted services ABOUT BENNIE Bennie is a national benefits broker, consultant, and technology firm, who brings a modern, tech-focused approach to benefits. Our mission is to help companies create a healthier workplace and build a better world.

About

WhenFree

Effortlessly share your availability without leaving conversations. This app integrates with your calendar to suggest and insert free times directly into emails, texts, and other apps. Customize your availability rules for various meeting types and time zones.

Highlights
  • Custom keyboard for sharing availability
  • Integrates with iPhone calendar
  • Supports multiple meeting types (Pro)
  • Time zone conversion (Pro)
  • Siri and Shortcuts integration
  • Private by design, no account needed
Features
Read full description

Someone asks "when are you free?" by email, text or chat. You leave the conversation, open your calendar, come back and type times from memory. WhenFree answers from inside the conversation: switch to its keyboard, tap the times that work, and the exact sentence is typed from your calendar: "Tue 2–2:30pm or Wed 10am work for me (CT)." No account, no booking page. Your calendar stays on your iPhone. THE KEYBOARD: IN ANY APP YOU TYPE Email, chat, messaging apps, your CRM, a web form: anything with a text field. Your open times sit in a row above a full QWERTY keyboard. Suggest picks three good times in one tap; "Not this" swaps one out. Day peek shows what is around a time before you offer it. Plain text, so it works with anyone on any phone or computer. The keyboard never opens other apps, never sends anything anywhere, and works without Full Access. IN MESSAGES: THEY TAP A TIME In Messages, tap +, then WhenFree. Your week appears as a board. Tap the tiles that work and send. If they also have WhenFree, they tap a time and it goes on both calendars. If they reply by text, tap "They replied — add it" and it goes on yours. FOR PEOPLE WHO OFFER TIMES ALL DAY Realtors and agents booking showings, recruiters lining up calls, tutors, consultants, freelancers, small-business owners, parents coordinating the week. YOUR RULES, APPLIED EVERYWHERE • Working hours per day, including evenings and weekends if you want them • Buffers before and after, so travel time is never offered • Minimum notice and a maximum number of meetings per day • Days off and public holidays skipped • Hold time keeps time free for you; it is never offered • Several calendars treated as busy; all-day events handled sensibly MEETING TYPES (PRO) A showing is not a call. Give each kind of meeting its own length, buffers and place. Tap the type, or type "showing" in your message and WhenFree picks it. The place goes on the booked event only, never in the message. WHEN THEY ARE SOMEWHERE ELSE (PRO) Send times in the other person's time zone. Offered times stay marked on your week until they answer, so you never offer the same slot to two people. SIRI, SHORTCUTS, WIDGET AND CONTROL CENTER Ask Siri "When am I free in WhenFree", or tap Copy free times on the widget or in Control Center, and paste anywhere. PRIVATE BY DESIGN No server, no WhenFree account. Your calendar, event titles and messages stay on your iPhone. The keyboard and the Messages extension have no network access at all. The app goes online only if you connect a Google or Outlook account, and then only to read when you're busy and, if you allow it, to add the bookings you make. No analytics, no trackers. App Store privacy label: Data Not Collected. WHAT IT CANNOT DO WhenFree does not book on the other person's behalf, does not send invitations, and does not read your conversations. PLANS Free: 3 sends a month from Messages plus 3 inserts a month from the keyboard, from one calendar, for the current week, using your working hours. WhenFree Pro removes the limit and unlocks every calendar, a month ahead, meeting types, times in their zone, offered times marked, and every rule. • Annual — $29.99/year • Monthly — $4.99/month • Lifetime — $49.99 once, no subscription All three unlock the same thing and support Family Sharing. Payment is charged to your Apple Account at confirmation of purchase. Subscriptions renew automatically unless cancelled at least 24 hours before the end of the current period; your account is charged for renewal within 24 hours before the end of the period. Manage or cancel in Settings › [your name] › Subscriptions. Terms of Use: https://dotdotdotapps.com/whenfree/terms Privacy Policy: https://dotdotdotapps.com/whenfree/privacy Requires iOS 26 or later and Calendar access. Works with any calendar account on your iPhone (iCloud, Google, Outlook/Exchange, and others). Calendar not on your iPhone? Connect Google or Outlook in Settings.

Screenshots

Bennie4 screens
WhenFree4 screens

Verdict

The call

The clearest difference is rating: WhenFree at 5.0 against Bennie's 4.5. WhenFree also leads on update cadence (daily vs monthly) and review sentiment (100% vs 90%). Bennie's advantage is in-app purchases (none vs 3) and ratings volume (69 vs 2). On price, ads and device support there is nothing between them.

Scored on Price · Rating · Positive reviews · Number of ratings · Update frequency · Ads · In-app purchases · Monetization · Best chart rank · Devices · Requires iOS

CostPrice · In-app purchases · Ads · Monetization

Both are free to download. WhenFree sells 3 in-app purchases, starting at $4.99 per month. Bennie asks for nothing beyond the download.

ReceptionRating · Positive reviews · Number of ratings

WhenFree holds the better App Store score, 5.0 against 4.5. That said, the two scores are not equally well evidenced: Bennie has 69 ratings behind it against 2, so its average is the more settled of the two. Written reviews point the same way: 90% of Bennie's written reviews are positive against 100% of WhenFree's.

UpkeepUpdate frequency

Bennie ships an update monthly, WhenFree daily. Both last shipped on November 13, 2026.

Scorecard7 real differences · 3 level
Bennie versus WhenFree: the parameters behind the verdict, then further details
ParameterBennieWhenFree
PriceFreeFree
Rating4.5 (69 ratings)5.0 (2 ratings) — better
Positive reviews90.0% of reviews100.0% of reviews — better
Number of ratings69 — better2
Update frequencyMonthlyDaily — better
AdsNoNo
In-app purchasesNo — betterYes
MonetizationFree — betterFreemium
DevicesiPhoneiPhone
Requires iOS16.4 — better26.0
Further details — not scored
Size100 MB32 MB
Age rating12+4+
DeveloperBennieDotdotdotapps LLC

Customer experience

Bennie

All ratings69 ratings
Positive87.0%
Neutral0.0%
Negative13.0%
Written reviews30 reviews
Positive90.0%
Neutral0.0%
Negative10.0%

WhenFree

All ratings2 ratings
Positive100.0%
Neutral0.0%
Negative0.0%
Written reviews2 reviews
Positive100.0%
Neutral0.0%
Negative0.0%

In-app purchases

None

Bennie

No in-app purchases

3 purchases

WhenFree

Subscriptions2
  • WhenFree Pro Monthly$4.991 Month
  • WhenFree Pro Annual$29.991 Year
One-time1
  • WhenFree Pro$49.99

Questions

Is Bennie free?
Bennie is free to download, with no in-app purchases.
Is WhenFree free?
WhenFree is free to download, with in-app purchases available.
Which has better reviews, Bennie or WhenFree?
WhenFree is rated higher. Bennie averages 4.5 out of 5 from 69 ratings, while WhenFree averages 5.0 from 2 ratings.
Do Bennie or WhenFree have ads?
Neither Bennie nor WhenFree shows ads.
Which is updated more often, Bennie or WhenFree?
Bennie ships an update monthly, and WhenFree daily. Most recently, Bennie was updated on November 13, 2026 and WhenFree on November 13, 2026.

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