diff --git a/src/org/labkey/test/components/domain/CalculatedColumnAssistantDialog.java b/src/org/labkey/test/components/domain/CalculatedColumnAssistantDialog.java
new file mode 100644
index 0000000000..ca94aa9f17
--- /dev/null
+++ b/src/org/labkey/test/components/domain/CalculatedColumnAssistantDialog.java
@@ -0,0 +1,180 @@
+package org.labkey.test.components.domain;
+
+import org.labkey.test.Locator;
+import org.labkey.test.WebDriverWrapper;
+import org.labkey.test.components.bootstrap.ModalDialog;
+import org.openqa.selenium.WebElement;
+
+import java.util.List;
+import java.util.stream.Collectors;
+
+/**
+ * Modal that opens when the user clicks the "AI Assistant" button inside the Calculation field options.
+ * Provides a chat-style interface where the user enters prompts and the assistant suggests expressions.
+ */
+public class CalculatedColumnAssistantDialog extends ModalDialog
+{
+    public static final String TITLE = "Expression AI Assistant";
+
+    private final DomainFieldRow _row;
+
+    public CalculatedColumnAssistantDialog(DomainFieldRow row, ModalDialogFinder finder)
+    {
+        super(finder);
+        _row = row;
+    }
+
+    public CalculatedColumnAssistantDialog(DomainFieldRow row)
+    {
+        this(row, new ModalDialogFinder(row.getDriver()).withTitle(TITLE));
+    }
+
+    /**
+     * Type the prompt into the textarea. The submit button stays disabled until non-empty text is present.
+     */
+    public CalculatedColumnAssistantDialog setPrompt(String prompt)
+    {
+        getWrapper().setFormElement(elementCache().promptInput, prompt);
+        WebDriverWrapper.waitFor(() -> elementCache().promptSubmitButton.isEnabled(),
+                "Prompt submit button did not become enabled.", 2_000);
+        return this;
+    }
+
+    public String getPrompt()
+    {
+        return getWrapper().getFormElement(elementCache().promptInput);
+    }
+
+    /**
+     * Click the submit (arrow) button. First waits for the "Thinking..." spinner to disappear (up to 60s)
+     * and then for a new assistant response to render (up to 10s).
+     */
+    public CalculatedColumnAssistantDialog submitPrompt()
+    {
+        int previousCount = getAssistantResponses().size();
+        elementCache().promptSubmitButton.click();
+        waitForThinkingSpinnerToDisappear();
+        WebDriverWrapper.waitFor(() -> getAssistantResponses().size() > previousCount,
+                "No new assistant response appeared in chat history.", 10_000);
+        return this;
+    }
+
+    private void waitForThinkingSpinnerToDisappear()
+    {
+        Locator spinner = Locator.tagWithClass("i", "fa-spinner");
+        // Spinner may not appear if the response is instantaneous; that's fine.
+        WebDriverWrapper.waitFor(() -> !spinner.existsIn(this), 60_000);
+    }
+
+    /**
+     * Convenience: type the prompt and submit it.
+     */
+    public CalculatedColumnAssistantDialog sendPrompt(String prompt)
+    {
+        return setPrompt(prompt).submitPrompt();
+    }
+
+    /**
+     * @return one entry per assistant response bubble (concatenated text of all its {@code .assistant-text} blocks),
+     * in chat order. Suggested-expression SQL is not included here — see {@link #getSuggestedExpressions()}.
+     */
+    public List<String> getAssistantResponses()
+    {
+        return Locator.tagWithClass("div", "chat-item").withClass("assistant-response")
+                .findElements(this).stream()
+                .map(WebElement::getText)
+                .collect(Collectors.toList());
+    }
+
+    /**
+     * @return text of the most recent assistant response, or empty string if there are none.
+     */
+    public String getLastAssistantResponse()
+    {
+        List<String> responses = getAssistantResponses();
+        return responses.isEmpty() ? "" : responses.get(responses.size() - 1);
+    }
+
+    /**
+     * @return every SQL expression suggested in the most recent assistant response, in display order.
+     * Usually a single entry, occasionally more.
+     */
+    public List<String> getSuggestedExpressions()
+    {
+        WebElement lastResponse = lastAssistantResponseElement();
+        if (lastResponse == null)
+            return List.of();
+        return Locator.tagWithClass("div", "assistant-expression")
+                .descendant(Locator.tag("code"))
+                .findElements(lastResponse).stream()
+                .map(WebElement::getText)
+                .collect(Collectors.toList());
+    }
+
+    /**
+     * @return the first SQL expression in the most recent assistant response, or empty string if none.
+     */
+    public String getFirstSuggestedExpression()
+    {
+        List<String> expressions = getSuggestedExpressions();
+        return expressions.isEmpty() ? "" : expressions.get(0);
+    }
+
+    /**
+     * Click "Apply Expression" on the first suggestion in the most recent assistant response.
+     * Returns the underlying field row (the dialog stays open; call {@link #clickEndChat()} to close it).
+     */
+    public DomainFieldRow applyFirstSuggestedExpression()
+    {
+        WebElement lastResponse = lastAssistantResponseElement();
+        if (lastResponse == null)
+            throw new IllegalStateException("No assistant response is available to apply.");
+        Locator.tagWithClass("div", "assistant-expression")
+                .descendant(Locator.tagWithClass("button", "clickable-text"))
+                .findElement(lastResponse)
+                .click();
+        return _row;
+    }
+
+    private WebElement lastAssistantResponseElement()
+    {
+        List<WebElement> responses = Locator.tagWithClass("div", "chat-item").withClass("assistant-response")
+                .findElements(this);
+        return responses.isEmpty() ? null : responses.get(responses.size() - 1);
+    }
+
+    /**
+     * Click "End Chat" to close the dialog.
+     */
+    public DomainFieldRow clickEndChat()
+    {
+        elementCache().endChatButton.click();
+        waitForClose();
+        return _row;
+    }
+
+    @Override
+    protected ElementCache newElementCache()
+    {
+        return new ElementCache();
+    }
+
+    @Override
+    protected ElementCache elementCache()
+    {
+        return (ElementCache) super.elementCache();
+    }
+
+    protected class ElementCache extends ModalDialog.ElementCache
+    {
+        final WebElement endChatButton = Locator.tagWithClass("button", "btn")
+                .withText("End Chat")
+                .findWhenNeeded(this);
+
+        final WebElement promptInput = Locator.tagWithClass("textarea", "prompt-input")
+                .findWhenNeeded(this);
+
+        final WebElement promptSubmitButton = Locator.tagWithClass("button", "prompt-button")
+                .findWhenNeeded(this);
+    }
+}
diff --git a/src/org/labkey/test/components/domain/DomainFieldRow.java b/src/org/labkey/test/components/domain/DomainFieldRow.java
index 107df90f36..d05c6fc9aa 100644
--- a/src/org/labkey/test/components/domain/DomainFieldRow.java
+++ b/src/org/labkey/test/components/domain/DomainFieldRow.java
@@ -1070,6 +1070,17 @@ public String getValueExpression()
         return getWrapper().getFormElement(elementCache().expressionInput);
     }
 
+    /**
+     * Click the "AI Assistant" button in the expanded Calculation field options and return the resulting dialog.
+     */
+    public CalculatedColumnAssistantDialog openAIAssistant()
+    {
+        if (!isExpanded())
+            expand();
+        elementCache().aiAssistantButton.click();
+        return new CalculatedColumnAssistantDialog(this);
+    }
+
     // advanced settings
 
     public DomainFieldRow showFieldOnDefaultView(boolean checked)
@@ -1763,6 +1774,7 @@ protected class ElementCache extends WebDriverComponent.ElementCache
         public final WebElement expressionStatusError = expressionStatusMsgLoc.descendant(Locator.tagWithClass("span", "error")).refindWhenNeeded(this);
         public final WebElement expressionStatusMsg = expressionStatusMsgLoc.childTag("div").refindWhenNeeded(this);
         public final WebElement expressionValidateLink = expressionStatusMsgLoc.child(Locator.tagWithClass("div", "validate-link")).refindWhenNeeded(this);
+        public final WebElement aiAssistantButton = Locator.tagWithClass("button", "btn").withText("AI Assistant").refindWhenNeeded(this);
 
         Locator.XPathLocator aliquotWarningAlert = Locator.tagWithClassContaining("div", "aliquot-alert-warning");