Manage AI conversations, history and context

History and context are not the same thing

This is why a model can seem to forget something you can still scroll up and read. Your archive kept it; the request that produced the answer did not include it verbatim. Documents and Active Notes attached to an earlier message are part of the conversation in the same way: later requests carry them until compaction summarizes them.

Context compaction, step by step

When a thread outgrows the context window it is being sent on, SideNote Pro does not simply drop the oldest messages. It compacts.

1. Keep the recent messages intactAt least the eight most recent are carried forward word for word, because recency is where most follow-up questions point.
2. Summarize the older contextSideNote Pro asks your configured model to produce a structured summary of the earlier part of the conversation.
3. Carry the summary forwardSubsequent requests include that summary in place of the original older messages.
4. Save the boundaryThe summary and the compaction boundary are stored in the thread, so reopening it later behaves consistently.
5. Keep every original message locallyCompaction changes what is sent. It never rewrites or deletes your local archive.

Setting the context window

Context window sits on the provider profile rather than on the application, because a small local model and a current hosted one can differ by two orders of magnitude. It has two modes: Auto, which is the right answer for almost everyone, and Custom, where you set the number yourself for every model that profile uses.

On Auto, SideNote Pro uses a 128,000-token default. If the provider reports a smaller context length for that exact model in its model-list response, the smaller limit is used, because sending more than a model can take fails outright. Auto never grows above 128K just because a model supports more: filling a huge window on every turn would make each request slower and more expensive for work that rarely needs it. Choose Custom if you want a different size.

The line under the control shows which rule is active. Default context size: 128k means Auto is using SideNote Pro's default; Provider-reported context size: 32,768 tokens means the provider reported a smaller limit for this model. Running Test & Load models is what lets Auto see a reported size when the provider exposes one, including the per-model input limits Anthropic publishes.

Settings › AI providers

Custom accepts 1,024 to 10,000,000 tokens and always wins over Auto. Use it when you know the model supports a different size, including a context window larger than 128K. The global Fallback context window setting that earlier versions had under History no longer exists.

Token counts here are estimates, based on text length plus a fixed allowance per message and image, rather than your provider's own tokenizer. SideNote Pro also keeps headroom rather than trying to fill every theoretical token, which is why a thread compacts a little before the arithmetic says it must.

Often the better fix is not a bigger window but a new thread. A conversation that has wandered through four topics carries three of them as dead weight into every request. Ctrl+N is cheap.

Finding and organising threads

Ctrl+H opens history, grouped into Pinned, Today, Yesterday, Previous 7 days and Older.

Search

runs full-text across titles and message content, so a thread can be found by something said in the middle of it.

Pin

the threads you return to. Pinned threads are exempt from retention pruning.

Rename

when the generated title turned out not to describe the conversation.

Delete

with confirmation.

Export to Markdown

for one thread.

Open and continue

with your draft and scroll position restored.

Titles are generated from your first message or attachment name, shortened to about 52 characters. That makes the first sentence you type worth a moment's thought: it becomes the label you will scan for weeks later. Organising AI conversations has more on this.

If a conclusion or next step is worth keeping visible without searching through the full thread, save it as a Takeaway. The card sits beside the conversation in a wide window, or behind the Takeaways button in the title bar, quoting the message it came from, and Jump to source takes you back to that message. All conversations searches the Takeaways of every thread at once.

Retention, protection and deletion

History off

Disable local history entirely.

Retention

Delete inactive threads after a number of days. 0 keeps everything indefinitely. Pinned threads are never pruned.

Encryption

Apply Windows DPAPI to the archive, binding it to your current Windows account. Local at-rest protection, not a portable password-based format.

Delete all history

Permanent removal of the archive.

A sensible default for most people: history on, retention at 90 days, pins for the threads worth keeping, encryption on if the machine is shared or portable.

Takeaways and their notes live inside their conversation, so all of this applies to them: deleting a thread, or letting retention remove it, deletes its Takeaways, and encryption covers them. Turning history off hides the Takeaways rail and stops new ones, but deletes none. Active Notes are kept apart from conversations: history off, retention and delete-all leave them alone, while encryption covers them too.

Settings › History

Settings › History

Exporting every conversation

1. Open Settings › HistoryExport all conversations… is in the same section as retention and protection.
2. Choose where to save the fileSomewhere private. SideNote Pro suggests a name with today's date, and does not let you save inside its own data folder.
3. Check the countWhen the file is written, SideNote Pro says how many conversations it holds.

What the file holds

The file is one JSON document holding every saved conversation as it was last saved: messages with their provider and model, Takeaways and their notes, images, the extracted text of documents, notes sent with a message, and each conversation's draft and system prompt choice. Attachments not yet sent and edits not yet saved are not included, and neither are your settings, API keys, Active Notes library, usage figures or folder indexes.

Export settings to move them to another PC

Move settings to another PC, at the end of Settings › General, has Export settings… and Import settings…. The file moves your setup, not your data.

Keys, prompts and folders

Enter your API keys again on the other PC. The file holds your prompts, writing context and folder paths as plain text, so treat it as private. Importing says what it will replace, and nothing changes until you choose Save in Settings; a folder the other PC has not indexed starts as not indexed.

Backing up

There is no cloud copy and no cross-device sync, so a backup is your responsibility. The archive lives under %LOCALAPPDATA%\SideNote Pro\, with your Active Notes beside it.

One caveat that matters: a DPAPI-protected archive is bound to the Windows account that created it. Copying the file to another machine or another account will not make it readable there. To read your conversations elsewhere, export them, all at once as JSON or one at a time as Markdown, rather than copying the file.