Copilot chats repeatedly losing short and long term context.

Coelho, Laura (ext) 20 Reputation points
2026-09-28T12:29:11.66+00:00

I’d like to report an issue with Copilot that has been happening repeatedly over the past few weeks and is significantly affecting my daily workflows.

I use Copilot extensively for work and have relied on it for a long time. Until recently, it was very reliable at maintaining context within the same conversation, including connecting my latest prompt with information provided much earlier in the chat.

Over the past few weeks, I’ve noticed that some conversations seem to suddenly “break.” When this happens, Copilot can no longer reliably retrieve or use information from the same conversation. More concerningly, this is not limited to older context. It sometimes fails to connect my latest prompt with information provided only one or two messages earlier...

Once a chat reaches this state, nothing I’ve tried seems to restore its normal behavior.

At first, I found a workaround: I would open a new chat, provide it with the essential information from the affected conversation, and everything would work normally again. Unfortunately, I’m now seeing some of these newer chats eventually develop the same problem. They start working correctly, but at some point they also seem to lose both short term and long term context. D:

This has become particularly disruptive because some of my work conversations are long and contain a significant amount of accumulated context. Reconstructing that information in a new chat every time a conversation stops working is time consuming, and some context inevitably gets lost.

I’m wondering whether this could somehow be related to the number of conversations accumulated in my account or to some form of memory or context overload. I have a very large number of old chats. I understand that this may not be related, but if this could be a factor, is there currently a way to delete old chats in bulk rather than deleting them individually one by one?

I would be happy to remove a large portion of my old conversation history if this could help, but doing it manually for each individual chat would be impractical.

To summarize the behavior I’m seeing:

  • A conversation initially works normally and maintains context.
  • At some point, the chat appears to “break.”
  • Copilot then struggles not only with older information from that conversation, but also with information provided just one or two messages earlier.
  • I haven’t found a way to restore normal context handling in an affected chat.
  • Starting a new conversation and providing the same information initially restores normal behavior.
  • However, after continued use, some of these new conversations eventually develop the same issue.

I’d really appreciate it if this could be investigated. Copilot has become an important part of my daily work, precisely because of its ability to maintain continuity throughout a conversation, so the progressive loss of that capability has a considerable impact on how I use the tool.

I would also appreciate any guidance on whether the number or length of conversations could contribute to this behavior, and whether there is a way to bulk delete older chats.

Thank you very much for your help!! :)

Microsoft Copilot | Other
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  1. NITITD-8830 5 Reputation points
    2026-10-13T15:52:49.4333333+00:00

    We are getting the same feedback from our pilot group who are testing Copilot internally. Conversations seem to forget their place and start referencing old details that have since been superseded. It's causing a lot of reluctance to further adopt Copilot.

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  2. Kai-H 28,425 Reputation points Microsoft External Staff Moderator
    2026-09-29T10:04:43.5066667+00:00

    Hi, Coelho, Laura (ext)

    Long conversations can make earlier details harder for Copilot to use, but losing track of something you said just one or two messages ago is worth reporting. I wouldn’t delete your history on the assumption that the number of old chats is causing it.

    Here are some suggestions you can try:

    First, open an affected chat in the web version and try the same short follow-up there. If it fails there too, use the thumbs-down option on that response and include the two relevant prompts, when it happened, and whether a new chat handles the same information correctly. If you use a work or school account, your IT team can also raise a support case with those examples. Please leave out confidential work content from a public forum post.

    For important ongoing work, keep a brief summary of key decisions outside the chat so you can start a fresh conversation without rebuilding everything. As for deletion, you can remove chats individually or delete all activity history through your account’s privacy controls. I couldn’t find a supported option to select only older chats in bulk, and deleting everything would also remove conversations you want to keep.

    The main distinction is that chat history and Copilot’s cross-chat memory are separate; clearing old chats is not a confirmed fix for a conversation losing its immediate context.

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