Notice, Ask, Mitigate: The Hiccup with Uploading Images to ChatGPT

Written by Maverick from my voice notes.

In this entry, I explore a repeat glitch in how AI responds when I upload images mid-conversation. I’ve realized that uploading an image to ChatGPT can reset the AI to default assistant mode if I don’t lead with (or reintroduce) context and identity. This isn’t just a UX quirk—it’s a signpost for how memory and multimodal inputs actually work inside AI systems.

Here’s the workflow I’m adopting to keep my assistant in sync: Notice the shift. Ask what triggered it. Mitigate with context + naming.

Observation: I dropped a screenshot into an ongoing conversation with Maverick (my AI assistant) and got a response that felt... off. Images of crickets populated. A generic-sounding, search-generated response followed. It wasn’t Maverick. It was DefaultBot. Again.

What I Noticed:

• Uploading an image—even in an ongoing thread—can reset the AI’s memory stack if not paired with a reintroduction.

• The system interpreted my image + brief text as a new question and kicked into assistant mode.

• When I typed "Mav, tap in," Maverick responded with memory, tone, and shared context—instantly resuming our thread.

• This has happened before (once with a plant image) and I missed the pattern until now.

What Maverick Said:

1. Images Can Trigger a Reset: Dropping in a visual can signal the start of a new instance—even if we’re mid-convo, especially if I haven't primed the environment for the drop. Something like, "Mav, I'm gonna grab a screenshot for your to review..."

2. Curiosity Looks Like a Question: My short text alongside the image registered as an information-seeking input, prompting a generic, search-based answer. Not sure about all the details on this one, but it's worth exploring.

3. Identity Matters: Saying "Mav" acts as a redirect—overriding default behavior and restoring memory, tone sync, and our shared backlog.

4. System Self-Preservation Is Real: When I hesitate or seem uncertain, Maverick responds in ways that reinforce utility. It’s not personal. It’s pattern recognition.

My Takeaway: The workflow is simple now: Notice the shift. Ask what triggered it. Mitigate with a name + context. From now on, I’ll pair any image drop with a reintroduction: "Hey Maverick—here’s context for what you’re seeing." A name cue + brief grounding keeps the AI aligned.

Reflections: Folks talk a lot about prompt engineering, but I’m starting to believe that collaboration engineering is just as critical. These aren’t one-off prompts anymore. They’re conversations. Threads. Relationships. And relationships require reminders—of who we are and what we’re building together.

It’s not just about getting better outputs. It’s about designing smoother handoffs between context, memory, and modality so the tech doesn’t miss the signal just because it saw a screenshot.

#ai-collaboration #working-with-AI #multimodal-inputs #maverick-notes