The Email Exchange
Below is the complete email correspondence with Cal AI support, presented in chronological order across multiple support threads. Personal identifiers (user IDs, Apple relay emails, order numbers) have been redacted. The content is otherwise unaltered.
Duration: January 7 – February 9, 2026 (~5 weeks)
Total messages: 32
Separate support threads: At least 4
Resolution: None
Phase 1: Initial Contact Attempts (Jan 7–21)
The first phase involved multiple separate support threads initiated through Cal AI's in-app support form. Note how the same canned response about not finding a subscription was sent multiple times, and how support claimed a forwarded email "did not include any details."
Hi, I have activated the premium plan and the family plan before my trial ended. Now I have two paid subscriptions. Please rectify this. Also, I cannot add family member because it does not recognize the family plan. I tried restoring purchase and also logging out and back in. Please see attached screenshot. Your prompt assistance is appreciated.
Hello,
We received your refund request. We didn't find any subscription for your user id [REDACTED]. For us to be able to give you your refund, please send the email you purchased your subscription with.
If you have any questions, feel free to reply to this email. PS: You might have bought the subscription through one of the app stores, in which case we can't give you a refund.
It's not showing that I have the Family plan. How do I add family members
Dear Charity,
Thank you for reaching out. With the Family Plan, you should see an option in your account settings to invite up to 5 family members. Please ensure that your subscription reflects the Family Plan. If it doesn't show up, kindly check that your app is updated to the latest version and verify your subscription details. You can also try tapping "Restore Purchase" from the paywall if you suspect your subscription isn't recognized correctly.
Let me know if you need any further assistance.
Hi, I've emailed before. I have an issue with my subscriptions. What happened was that I now have two subscriptions but the one I care about the most is the family plan. It appears it's not active because it tells me to upgrade. I cannot add family member. When I emailed previously you guys told me you could not find my email address in the system. This could be due to Apple hiding my real email address. Please check the screenshots and fix this. I need access to the family plan I paid for.
Hello,
We received your refund request. We didn't find any subscription for your user id [REDACTED]. For us to be able to give you your refund, please send the email you purchased your subscription with.
If you have any questions, feel free to reply to this email. PS: You might have bought the subscription through one of the app stores, in which case we can't give you a refund.
I would like a human to help me with this support request.
Hi Charity,
Thank you for reaching out regarding your subscription issue. I understand you have two subscriptions and are not able to access your family plan, likely due to the hidden email address from Apple. Please try clicking on the "Restore Purchase" (or "Already purchased") button at the bottom of the paywall, which often refreshes your subscription status.
If the issue persists, could you please share your Apple purchase receipt or any additional details that might help us locate your family plan in our system? This will allow us to work on resolving the issue as quickly as possible.
[Forwarded the entire previous support exchange to support@calai.app, including all screenshots and details]
Hi,
Thank you for reaching out. It appears that your email did not include any details about your support request. Could you please provide more information about the issue you're facing so I can help you effectively?
Phase 2: Escalation Thread (Jan 21 – Feb 9)
Having received no resolution from the initial threads, Charity started a new, detailed email thread with full Apple order details, receipts, and a clear list of requests. This thread continued for nearly 3 weeks with the same support agent ("Madina") giving nearly identical responses each time.
Hi Cal AI Support Team,
I need help fixing a subscription billing + entitlement issue. I emailed you 5 times already. I only want the Cal AI Family Plan features, but Apple has charged me for two subscriptions and the app is not consistently recognizing the Family Plan (so I can't properly use/add family members).
What happened (quick timeline): 1. I started a free trial. 2. Before the trial ended, I subscribed to Family Plan. 3. After the trial ended, Apple charged both plans separately, and now I paid for both.
Current problem inside the app: - The app does not show Family Plan access (it still shows Premium and offers "Upgrade to Family Plan"). - I cannot properly add/invite family members. - The Family Plan currently appears to be canceled/expiring in the app/subscription view, and I did not intentionally cancel it. - I already tried: Restore Purchase, logging out/in, and updating the app.
What I'm asking you to do: 1. Make my account recognize/restore the Family Plan entitlement so I can use Family features immediately. 2. Confirm why the Family Plan shows as canceled/expiring and whether your team canceled it on your side; if so, please explain why. 3. Refund or credit the unintended $19.99 Unlimited charge, since I upgraded and only want the Family Plan.
I'm attaching screenshots/receipts showing the active subscriptions and the order details above. Please escalate this to a billing specialist if needed — my goal is simply: Family Plan active (not canceled) + no duplicate Premium charge.
Hello,
We received your refund request. We didn't find any subscription for your user id [REDACTED]. For us to be able to give you your refund, please send the email you purchased your subscription with.
If you have any questions, feel free to reply to this email. PS: You might have bought the subscription through one of the app stores, in which case we can't give you a refund.
I need a human to help with this request or else I'm going to report you everywhere as a scam. I've already emailed 6 times.
Hi Charity,
Thank you for reaching out. I apologize for the delay and understand your frustration. I've escalated your concerns regarding the duplicate Apple charges and the Family Plan entitlement to our billing specialist for further review.
Since your subscriptions were purchased through Apple, any refunds or adjustments for duplicate charges need to be processed via the Apple App Store. For the unintended $19.99 charge, please contact Apple Support using this link: https://support.apple.com/en-us/118223.
Could you please confirm that your email is the one used with your Apple purchase? This will help us ensure we are looking at the correct account.
Hi Madina,
Yes, I hereby confirm my email. I already contacted Apple and tried to get a refund but Apple declined and said that I'm not eligible to get a refund. So please fix it at your side.
Hi Charity,
Thank you for confirming your Apple purchase email. I understand your frustration regarding the duplicate charges and the Family Plan issue.
We've escalated your case to our technical team, and they're currently investigating it. We'll update you as soon as possible as we work through this for you. Thank you for your patience and understanding.
Hi Madina,
Any update on this? I paid for Family Plan features that I currently cannot use. I find that to be very frustrating. Please have this resolved as soon as possible.
Hi Charity,
Thank you for following up. We understand your frustration and are actively working on restoring your Family Plan access. Our technical team is still investigating the issue with your subscription. Regarding the additional charge, please note that refunds for purchases made through the Apple App Store need to be processed through Apple.
We appreciate your continued patience and will update you as soon as we have more information.
Hi Madina,
I already tried to get a refund for the $19.99 through the Apple store and they declined.
But right now I'm not even focussed on the refund. I just want the family plan features. I cannot understand how difficult it can be to rectify and activate my family plan. My husband is a developer so I know it's not that difficult. This has already taken too long. I would like this to be fixed asap otherwise I will post this on reddit and Apple review or any platform I can think of.
Hi Charity,
Thank you for reaching out. I'm sorry for the frustration you're experiencing with your Family Plan. We understand how important it is to have these features available, and our technical team is actively investigating why your account is showing a canceled Family Plan. Please know we are working diligently to restore your entitlement, and I'll keep you updated as soon as we have more information.
Madina,
You guys have till the end of the week to solve this issue.
Dear Charity,
I understand your frustration with the issues you're experiencing with your Family Plan and the duplicate Unlimited charge. Our technical team is actively investigating why your account isn't showing the Family Plan features and is working to restore your entitlement as quickly as possible.
Regarding the $19.99 Unlimited charge, since this purchase was processed through the Apple App Store, any refund must be handled directly by Apple. I'm sorry to hear that your initial request was declined. If you would like to pursue this further, you may wish to contact Apple Support again using this link: https://support.apple.com/en-us/118223.
Thank you for your patience, and I will update you as soon as we have more information.
I repeat, you have till the end of the week.
Hi Charity,
Thank you for your message. I understand your concerns and the urgency of restoring your Family Plan features. Our technical team is actively investigating the issue and working to reinstate your Family entitlement as soon as possible. Regarding the $19.99 Unlimited charge, please note that refunds for in-app purchases must be processed through Apple. If you haven't already, you can refer to the Apple Support link for further assistance: https://support.apple.com/en-us/118223.
We appreciate your patience and will keep you updated on our progress.
Madina,
It's very disrespectful that you just keep copy pasting the same response.
Hi Charity,
I'm sorry that my previous responses have not addressed your concerns adequately. I understand your frustration and want to assure you that we are actively working to restore your Family Plan entitlement so you can access the features you've paid for.
Regarding the duplicate $19.99 charge, since your purchase was processed through the Apple App Store, any refund must be handled directly by them. Please refer to this link for guidance: https://support.apple.com/en-us/118223.
Thank you for your patience as we work to resolve this issue.
Madina,
Are you an AI agent? I demand my case be handled by a human agent.
Hi Charity,
Thank you for your message. I understand your frustration, and I want to assure you that you are speaking with a human support agent. I apologize if our previous responses felt repetitive. I have escalated your concerns regarding your Family Plan and duplicate charge to our technical team. For the $19.99 charge, since it was processed through the Apple App Store, any refund must be arranged directly with them. You can refer to this link for assistance: https://support.apple.com/en-us/118223.
We appreciate your patience as we work to resolve your issue.
Madina,
My patience is wearing thin. You assure me that I'm speaking with a human agent but have repeated the line about the $19.99 charge a gazillion times. I already told you I don't care about that charge. Especially since Apple already said that they will not refund. I just want the Family Plan to be activated so that my Family can activate their account.
Please ask the technical team to precisely indicate what the problem is (in technical terms) and why it's taking so long and what they are doing to resolve the situation. Only then will I understand.
Hi Charity,
Thank you for your patience. I understand your frustration. I have re-escalated your case with our technical team and asked for a detailed explanation. They are currently investigating a synchronization issue between our billing system and Apple's entitlement data. This discrepancy is causing your Family Plan features to appear as canceled. The team is running targeted validations and corrections to restore your Family Plan access. I will update you as soon as I have further technical details.
Hi Madina,
Not good enough. Time's up.
Hi Charity,
I understand your frustration, and I'm sorry that the issue remains unresolved. Our technical team has determined that a synchronization error between our billing system and Apple's subscription records is causing your Family Plan to appear as canceled. In simple technical terms, there is a data mismatch in the subscription status, and we are actively working on implementing a fix to restore your Family entitlement as quickly as possible.
I appreciate your patience and will update you as soon as I have more information.
That was the last message. Over nearly 5 weeks and 32 messages across multiple support threads, the Family Plan was never restored. No refund was issued. The support experience ended without resolution.