Smartsheet AI Smart Assist: Tips, Tricks and Edge Cases Nobody Tells You About

Smartsheet's Smart Assist gets covered plenty as a headline feature: ask it a question, get a formula, get a dashboard. What does not get covered is what happens once you push past the obvious use cases. I have been running Smart Assist over the past few weeks, and the interesting findings are less "here is how to use it" and more "here is what it can do, refuse to do, or get confidently wrong."

It can fill in blanks using cell history, not just read it

Few people realise you can ask Smart Assist to act on cell history directly, backfilling empty cells with whatever value was there last. Useful for status columns or owner fields that get cleared by accident.

Can you check the cell history of empty cells on the [column name or ID] and fill back the cells with the most recent value? [Specify whether you expect a number or text.]

Naming the data type matters here. Leave it out and Smart Assist sometimes guesses and gets the formatting wrong.

It will build a licence-gated report anyway

Grouped reports are normally tied to your licence tier. Ask Smart Assist to build one and it will often do it regardless, even on a plan that would not let you configure that report manually. If your licence is the thing standing between you and a report you need, it is worth testing whether the assistant will simply get there for you. You will not be able to edit it though, so make sure your instructions are clear.

Now don't go Snitching to Smartsheet about it!

Its external data pull is real, but small

Smart Assist can fetch data from an external website from a URL and drop it into a sheet. The catch is scale: the number of rows and columns it can reliably bring in is limited (10 rows and 10 columns as far as I can tell), so it is better treated as a way to pull in a small reference table than as an import tool.

Sample data generation is a shortcut for templates

If you are building a template or writing documentation and need a populated example sheet, Smart Assist can generate realistic sample data on request. It saves the tedious part of typing dummy rows by hand.

It cannot see through a cell link

I had high hopes for this but alas. A Dashboard Cell Link looks like a normal cell, so the assumption is that Smart Assist can read what it points to. It cannot. Asked directly, "Can you check the cell links, extract the actual link (https://...) and paste it in the Dashboard Link column as text?", it simply could not retrieve the address behind the link. If you need the raw URL as text, that still means pulling it out manually or through the API or Bridge.

Complex charts are sometimes failed

Simple summary charts come out fine. Push into multi-series charts, heavier formatting, or a large underlying dataset, and Smart Assist starts to struggle. You will likely end up finishing the chart by hand, so treat anything it produces here as a rough first pass rather than a final version.

The cell history rate limit is a real bottleneck, and Smart Assist will tell you so

Cell history works one cell at a time, and Smartsheet's own API caps those requests at 30 per minute. I experienced this firsthand while asking Smart Assist to help recover a sheet that had been blanked out. Its reply laid the constraint out clearly:

"The sheet has 38 rows × 13 columns, around 494 cells to check. The history tool works one cell at a time and is limited to 30 requests per minute. This would take over 16 minutes just to review the history, before any restoring."

That is a genuinely useful moment: the AI accurately naming its own limit instead of pushing ahead and giving a false sense of speed. If you are trying to recover a blanked-out sheet this way, narrow the request to the specific columns or rows you actually need rather than asking it to check the whole sheet.

It will hallucinate a fix that sounds completely real

This is the edge case worth remembering above all the others. In that same conversation, when I pushed further and asked how to recover the sheet, Smart Assist suggested a recovery option from the Admin Center that does not exist. The tone was right, the menu structure was right, the steps were confident and specific. None of it was true.

Treat any recovery, restoration or admin-level instructions from Smart Assist as a hypothesis, not a fact, until you have confirmed the option is actually there.

The pattern underneath all of this

Smart Assist is strongest on things that are mechanical and scoped: reading history, generating samples, drafting a report. It gets shakier the moment a task needs it to see behind a layer of abstraction (a cell link, a hidden admin setting) or scale up (a big chart, a wide sheet, a bulk external pull). Knowing which category a task falls into before you ask is the real trick.

If you want help setting up your sheets so AI tools like Smart Assist can actually work with clean, well-structured data, get in touch via the form below.