Overview
The Cutover AI Assistant is an in-product, conversational assistant that helps you understand, manage, and improve runbooks, templates, and snippets using natural language. Instead of manually reviewing tasks, timings, and execution history, you can ask questions, identify risks, summarize outcomes, view a gantt chart and make planning-stage updates directly through chat.
The AI Assistant supports teams during planning, live execution, and incident response—whether you’re recovering from an incident, responding to an outage, migrating systems, or executing a release. It appears directly within the runbook task list UI and is powered by Cutover’s AI Service
Note: The Cutover AI Assistant is enabled on request. Please contact your Customer Success Manager (CSM) to discuss access.
Key Benefits
Quickly understand the status of complex workflows
Reduce time spent manually reviewing tasks and history
Identify bottlenecks, delays, and optimization opportunities
Make updates and improvements using natural language
Support faster incident response and improved RTO/MTTR outcomes
Note: The Cutover AI Assistant builds on the capabilities previously available in AI Improve, bringing them into a single conversational experience with expanded context, broader coverage, and more flexible interactions.
Note: Responses provided by the AI Assistant are AI-generated and may contain inaccuracies or incomplete information. We recommend reviewing and validating outputs before acting on them, especially when making operational or planning decisions.
Accessing the AI Assistant
To open and use the AI Assistant:
Open a runbook, template, or snippet.
Click the AI Assistant icon on the right-hand side of the screen.
3. Enter a question in natural language or select one of the suggested prompts.
While generating a response, the AI Assistant displays the tools it is using to gather information and perform actions.
Click the lightning icon in the bottom-left corner of the AI Assistant to view prompt categories. Suggested prompts are organized into contextual categories that adapt based on your runbook's stage.
Select a category to view example prompts. During planning, prompts are grouped into areas such as summaries, readiness, risks, timelines, ownership, and communications. During execution, additional categories are available for issue management and decision support, helping you quickly find relevant prompts.
Select a prompt to run it in the AI Assistant.
4. Retry an AI Assistant response
If an AI Assistant response fails, is incomplete, or isn’t useful, you can use Retry to generate a new response. Hover over the message and select Retry—the previous response will be replaced with a new one for the same prompt.
If retrying an earlier message, the view will return to that prompt. If a response was interrupted, you can reopen the assistant and retry to generate a complete response.
Retry is only available once any current response has finished and won’t appear if the conversation has been deleted.
5. Copy an AI Assistant response
You can easily copy an AI Assistant response to use elsewhere. Simply hover over the assistant message in the AI Assistant panel and select Copy. The full response will be copied to your clipboard, ready to paste where needed.
Permissions and Governance
The AI Assistant cannot elevate your existing Cutover permissions.
Users with read-only access can query and summarize but cannot apply changes.
All updates made by the Assistant are treated like standard edits and are recorded in the audit log, including details of what was changed, when the change was made, and who initiated it.
AI Assistant chats are not stored. Chats are retained only in your local browser storage for the duration of your current session and are not saved to the Cutover database or servers.
Chats can be exported as a .txt file or deleted at any time during the current session. Exported files are titled AI Assistant Chat Runbook followed by the runbook number. The Export and Delete options are available from More options at the top of the AI Assistant when a chat exists.
Approving AI Assistant changes
When a prompt requests a change that requires user approval, a confirmation dialog is displayed. You can choose to:
Approve this request only – approves and applies the requested tool call.
Allow '<tool name>' for this session - automatically approves future tool calls of the same type for the current chat session. In the image shown below this would be 'Update Task'.
Allow all actions for this session – automatically approves all tool call requests for the current chat session.
If you choose Allow '<tool name>' for this session or Allow all actions for this session, the approval preference remains active until you delete the conversation or start a new chat session.
Note: Tools called that have been approved for the duration of the session display an 'Auto-approved' label in the conversation.
If you select Reject, the requested action is cancelled and no changes are made.
What the AI Assistant can do
The AI Assistant provides a consistent set of capabilities across runbooks, templates, and snippets, with behavior tailored to each item type. AI-generated analysis is presented using recognizable user and team names where applicable, helping make insights easier to understand and act on.
1. Summarize Structure, Status, and Risk
The AI Assistant can summarize workflows and highlight potential risks by analyzing RTO and RTA metrics, planned and actual task timings, task types and dependencies, sequencing, and overall runbook structure, including streams.
Example prompts
“Summarize this runbook and highlight any timing risks.”
“Which tasks are on the critical path?”
“What is the goal of this workflow?”
2. Analyze Historical Performance (Templates Only)
When working with templates that have been executed multiple times, the AI Assistant can analyze historical performance to identify trends, recurring delays, and areas of risk. It provides a summary of past executions along with recommendations to improve future runs.
Example prompt
“Have runbooks created from this template met their RTO?”
3. Review Audit History and Governance
The AI Assistant can query the audit log to help you quickly locate key events such as pauses, approvals, and other significant actions, without manually searching through logs. This supports governance, compliance, and post-event reviews.
Example prompts
“When was the runbook paused and for how long?”
“Who approved this template and when?”
4. Make Planning-Stage Updates via AI
If you have edit permissions, you can ask the AI Assistant to make planning-stage changes using natural language. This includes updating task dependencies and durations, modifying planned start and end times, setting or updating RTO start and end tasks, reassigning tasks to streams, changing task types, managing tasks, updating task settings such as auto-start or custom fields, and editing the message body and recipients of existing Email and SMS tasks. All changes made by the Assistant are recorded in the audit log.
Example prompts
“Set Task 10 to start after Task 5 finishes.”
“Change the duration of Task 12 to 30 minutes.”
“Add a new task after Task 5 called ‘Verify application health’ with a duration of 15 minutes.”
Note: All changes made by the Assistant are recorded in the audit log.
5. Support Live Incident Response (Runbooks Only)
During live incidents or major events, the AI Assistant helps responders quickly understand the current situation and determine next steps by summarizing runbook status, recent activity, task progress, and identified resolution steps.
Example prompts
“What’s going on with this incident?”
“Which tasks are currently blocking progress?”
“What do we need to do to move forward?”
How the AI Assistant works with Runbooks, Templates, and Snippets
Using the AI Assistant with Runbooks
When working with runbooks, the AI Assistant supports both planning and live execution. In addition to summarization and audit review, it enables planning-stage updates and real-time incident support.
Common runbook prompts
“Summarize recent activity in this runbook.”
“Where are the biggest timing risks?”
“What should we focus on next?”
Using the AI Assistant with Templates
With templates, the AI Assistant focuses on historical analysis and future improvement. It does not modify past executions.
Common template prompts
“Summarize this template.”
“Where do executions typically experience delays?”
“What improvements would you recommend for future runs?”
Using the AI Assistant with Snippets
When used with snippets, the AI Assistant helps ensure reusable task groups are clear, complete, and ready for reuse.
You can:
Summarize the purpose and structure of a snippet
Review task sequencing and completeness
Rename or update tasks during the draft stage
Ensure snippets maintain a consistent structure, naming convention and content
Common snippet prompts
“What does this snippet do?”
“Suggest improvements to this snippet.”
“Rename Task 3 to ‘Confirm rollback readiness’.”
Bulk updates with the AI Assistant
The AI Assistant can apply changes across multiple tasks using natural language, helping you update large plans more quickly and consistently.
Example Bulk Update Prompts
“Delete Tasks 20–25.”
“Change the duration of all Testing tasks to 30 minutes.”
“Move Tasks 10 through 15 to the Application stream.”
“Set auto-start for all Business Validation tasks.”
Further information
For further information, see our AI Assistant video here.
