Meet Oscar

Product details
HedonistEntrepreneur

Verified purchaser

Deals bought: 206Member since: Oct 2011
5 stars
5 stars
Dec 16, 2025

Strong Email Assistant Once Properly Trained — One Small UX Gap

Overall, OSCAR does a very solid job provided you train it properly.

If you give it:

- Emails that are genuinely representative of your tone and style, and
- A sufficient set of supporting documents so it understands what you’re about,

then the output quality improves markedly. Once trained, it produces emails that are consistent, relevant, and usable without any or only very minimal rewriting. In that respect, it performs as well as any AI email assistant I’ve used, including ChatGPT-style workflows. Possibly better and time will be the best judge of that.

So far, I’m happy with the results to give it five tacos.

The one annoyance (and it’s a real one) ....Signature handling is very limited.

You can enter your name, position, and company, but OSCAR simply drops this as plain text at the bottom of the email. It does not:

- Use your existing Gmail / Google Workspace signature, or
- Allow you to paste HTML from a signature manager (for example, NewOldStamp, which I also bought on AppSumo).

That means I’m still copying the Oscar output, deleting the draft Oscar created and then pasting the Oscar output into a newly initiated response so that my signature is included. It’s not a deal-breaker, but it is friction that shouldn’t exist in 2025.

I’ve already submitted this as a feature request, so hopefully it’s picked up quickly.

Comparison context:
Functionally, this is similar to using ChatGPT or Google Workspace AI for email drafting. The difference is that OSCAR becomes more effective more quickly because you can train it directly with your real emails and documents, rather than relying on prompts alone (ChatGPT) or generating emails from the deep dark murky muddy abyss of an inbox with nearly 20 years of rotting and festering email history to feed off (Workspace GMail AI assistant) ... yep I've been with Google Apps/Suite/Workspace since August 2006)

Bottom line:
Strong product. Good results when trained properly. One clear UX gap around email signatures. If that’s addressed, it becomes an easy recommendation.

Founder Team
Giovanni_Brees

Giovanni_Brees

Edited Dec 17, 2025

Wow, thanks for the 5 tacos and the thorough breakdown!

I had a good laugh at your description of the "festering email history" in Google Workspace :). That is exactly the problem we wanted to solve by allowing you to curate what Meet Oscar learns from.

On to the critique: Message received. Since you’ve already submitted the request (thank you!), we are looking into how to implement HTML pasting. We want Meet Oscar to be an "easy recommendation" for you, so we are going to work hard to close that gap.

Thanks again for the five tacos 🌮

Update December 17: We have implemented the HTML signature ;) - thank you for giving the great review, and suggestion. This feature is now available to all users!

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