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create-mail-attachment-upload-session

Destructive

Create an upload session to attach large files (3-150 MB) to Outlook messages or events, returning a pre-authenticated URL for iterative byte range uploads.

Instructions

Create an upload session that allows an app to iteratively upload ranges of a file, so as to attach the file to the specified Outlook item. The item can be a message or event. Use this approach to attach a file if the file size is between 3 MB and 150 MB. To attach a file that's smaller than 3 MB, do a POST operation on the attachments navigation property of the Outlook item; see how to do this for a message or for an event. As part of the response, this action returns an upload URL that you can use in subsequent sequential PUT queries. Request headers for each PUT operation let you specify the exact range of bytes to be uploaded. This allows transfer to be resumed, in case the network connection is dropped during upload. The following are the steps to attach a file to an Outlook item using an upload session: See attach large files to Outlook messages or events for an example.

💡 TIP: For large attachments (3-150MB). Body: { AttachmentItem: { attachmentType: 'file', name: 'report.pdf', size: 5000000 } }. Returns a pre-authenticated uploadUrl for direct PUT of file bytes.

Input Schema

TableJSON Schema
NameRequiredDescriptionDefault
bodyYes
messageIdYesPath parameter: messageId
includeHeadersNoInclude response headers (including ETag) in the response metadata
excludeResponseNoExclude the full response body and only return success or failure indication
Behavior4/5

Does the description disclose side effects, auth requirements, rate limits, or destructive behavior?

Annotations indicate destructive hint, but description adds value by explaining the iterative upload process, resumability, and return of upload URL. However, lacks details on potential side effects (e.g., interim storage) and authentication specifics beyond basic flow.

Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

Conciseness4/5

Is the description appropriately sized, front-loaded, and free of redundancy?

Description is moderately concise and well-structured. It front-loads the core purpose, follows with usage constraints, and ends with a helpful tip. Each sentence adds distinct value, though slightly verbose.

Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

Completeness4/5

Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

Given the complexity of an upload session tool, the description covers key aspects: usage scenario, size constraints, response content (uploadUrl), and reference to subsequent steps. Lacks explicit return schema but mentions the URL and example, which is sufficient for an experienced agent.

Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

Parameters4/5

Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

Schema provides basic parameter types, but description adds critical context for the 'body' parameter with an example snippet showing required fields (attachmentType, name, size). This compensates for schema's generic definition (additionalProperties: true). Other parameters are sufficiently described in schema.

Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

Purpose5/5

Does the description clearly state what the tool does and how it differs from similar tools?

Description clearly states the tool creates an upload session for iterative file upload to attach to Outlook items. It specifies file size thresholds (3-150 MB) and contrasts with simpler attachment method for smaller files, distinguishing it from 'add-mail-attachment' sibling.

Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

Usage Guidelines5/5

Does the description explain when to use this tool, when not to, or what alternatives exist?

Explicitly states when to use (files 3-150 MB) and when not to use (files <3 MB: use POST on attachments navigation). Provides step-by-step reference and a quick tip with example body format, guiding correct invocation.

Agents often have multiple tools that could apply. Explicit usage guidance like "use X instead of Y when Z" prevents misuse.

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