# Medicare on Your Terms — Decision tools, dates & costs > Medicare enrollment deadline calculator and cost estimator. (iPhone/iPad app by Resting Sycamore Advisors LLC.) - Source: https://appshunter.io/ios/app/medicare-on-your-terms/id6794431631 (this page in markdown: same URL + `.md`) - Developer: [Resting Sycamore Advisors LLC](https://appshunter.io/developer/6794431633) - Category: Medical, Finance - Price: Free - Rating: 5.00/5 from 1 App Store ratings - Age rating: 4+ - Requires: iOS 18.0 · 4 MB - Languages: American English - Released: 2026-08-28 - Data updated: 2026-10-01 - Monetization: free ## What is Medicare on Your Terms? Medicare comes with deadlines. Miss one and the penalty can follow you for as long as you have coverage. This app helps you find the dates and numbers that apply to you, before they turn into a problem. Seventeen tools, in plain language: WHEN TO SIGN UP Your Initial Enrollment Period is a fixed seven-month window tied to your 65th birthday. Miss it and you could wait months for coverage to start while paying a penalty for the rest of your life. Check your window, see whether a life event opens another one, and find out whether you need to sign up at all right now. WHAT A DELAY COULD COST Part B and Part D late penalties are permanent. They do not expire and they are not forgiven. Estimate what a gap would add to your monthly premium, check whether your income two years ago triggers an IRMAA surcharge, and see whether Part A is premium-free based on a work record. COVERAGE AND TIMING Your Medigap open enrollment is a one-time, six-month window. Inside it, no insurer can turn you down or charge you more for your health history. Once it passes, those protections are gone. Check where you stand, and see when you can switch plans. STILL WORKING COBRA is not coverage based on current employment. Choosing it over Medicare at 65 can lock in permanent Part B and Part D penalties. Sort out how job coverage, COBRA, or retiree coverage affects your timing before you decide. STAYING ORGANIZED Set reminders for deadlines that matter. Gather the documents you need before an appointment, so a time-sensitive window does not pass while you look for paperwork. Work through a readiness checklist if you are helping a parent. AFTER YOU ENROLL The Medicare Prescription Payment Plan does not lower your drug costs. It spreads what you owe across monthly payments, so a deductible reset does not land as one large January bill. Every Part D plan is now required to offer it. WHAT THIS APP DOES NOT DO It does not compare every Medicare plan. It does not recommend a plan. It does not replace Medicare, Social Security, your employer, a tax professional, or a licensed agent's advice. It is a set of calculators and checklists to help you understand your own situation before you make a decision. YOUR INFORMATION STAYS ON YOUR PHONE No account. No sign-up. No password. The math happens on your device. If you save a result, it stays on your phone, and you can delete it whenever you want. There is no advertising software, no analytics software, and no third-party trackers in this app. The app never asks for your Medicare number, Social Security number, bank details, doctor names, or prescriptions. It asks for the smallest thing that will do the job, like a birth month or a ZIP code. Once a year it downloads updated Medicare figures so the math stays current. That request sends nothing about you. ABOUT US If you want a person to look at your situation, the app can open an email or text draft addressed to Peter. You read it and decide whether to send it. Nothing is sent automatically. Resting Sycamore Advisors is a private, licensed insurance agency. We are not affiliated with or endorsed by Medicare, the Centers for Medicare & Medicaid Services (CMS), the Social Security Administration, or any other government agency. We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov, 1-800-MEDICARE (TTY 711), or your local State Health Insurance Program (SHIP) to get information on all of your options. Participating sales agencies represent Medicare Advantage [HMO, PPO, PFFS, and PDP] organizations that are contracted with Medicare. Enrollment depends on the plan's contract renewal. Everything in this app is for educational purposes and does not constitute an endorsement of any specific plan or provider. ## Key features - Enrollment deadline calculator - Late penalty estimator - IRMAA surcharge calculation - Medigap open enrollment tracking - Job coverage impact analysis - Deadline reminders - Readiness checklist ## Is Medicare on Your Terms safe? Not enough ratings yet to assess Medicare on Your Terms. ## Is Medicare on Your Terms legit? Medicare on Your Terms has limited verification signals. The AppsHunter Legitimacy Score for Medicare on Your Terms is 58 out of 100 points across 7 verification signals from App Store and developer data. ## Frequently asked questions about Medicare on Your Terms ### What is Sycamore Medicare Guide? Sycamore Medicare Guide is a free medical app designed to help users understand Medicare enrollment deadlines and potential costs. It offers various tools and calculators to assist with informed decision-making regarding Medicare plans. ### Does Sycamore Medicare Guide compare Medicare plans? No, Sycamore Medicare Guide does not compare every Medicare plan or recommend specific plans. Its primary function is to provide calculators and checklists to help users understand their personal situation before making decisions. ### Is Sycamore Medicare Guide free to use? Yes, Sycamore Medicare Guide is completely free to use. The app is available at no cost and does not require any in-app purchases. ### Does Sycamore Medicare Guide have ads? No, Sycamore Medicare Guide is ad-free. It does not contain any advertising software, analytics software, or third-party trackers, ensuring a private user experience. ### What personal information does Sycamore Medicare Guide collect? Sycamore Medicare Guide collects minimal personal information, only asking for the smallest data points necessary for calculations, such as a birth month or ZIP code. It never asks for your Medicare number, Social Security number, or bank details. ### How often is Sycamore Medicare Guide updated? Sycamore Medicare Guide downloads updated Medicare figures once a year to ensure the calculations remain current. The app was last updated on 2026-08-28 with version 1.0. ### What devices is Sycamore Medicare Guide available on? Currently, Sycamore Medicare Guide is available on iPhone devices. The app has an age rating of 4+. ### Can I get help from a person through Sycamore Medicare Guide? While Sycamore Medicare Guide is a self-service tool, it can help you draft an email or text message to Peter at Resting Sycamore Advisors LLC if you wish to discuss your situation with a person. You can then decide whether to send the drafted message. ## Version history (last 2 releases) ### 1.2 — 2026-09-02 New name, same free tools. Questions now come one at a time, with big buttons and a clear sense of where you are, instead of one long form. Every answer shows where the information came from and when it was last checked. Your answers still stay on your phone. Why it's built this way: it leads with the name change since returning users will notice that first, describes the change in terms of what they'll feel rather than what we built, and closes on privacy because that's the app's strongest promise. "Free" is worth keeping — it's in your promotional text and it's a real differentiator. ### 1.0 — 2026-08-28 No release notes. ## Apps similar to Medicare on Your Terms | App | Rating | Price | Category | | --- | --- | --- | --- | | [Medicare Broker](https://appshunter.io/ios/app/medicare-broker/id6473723634) | 5.0 (10) | Free | Medical | | [Medicare PlanFinder®](https://appshunter.io/ios/app/medicare-planfinder/id1475620704) | 5.0 (1) | Free | Medical | --- *Data collected daily from the US App Store and indexed by [AppsHunter](https://appshunter.io/). User reviews are verbatim App Store reviews. Ratings, prices and chart positions refresh continuously; this snapshot is from 2026-10-01.*