# Check email recipients and attachments Canonical page: https://agents.paretoid.com/workflows/check-email-recipients-and-attachments/ Category: Operations & Reporting Practice relevance: cross-practice. A general operational method. Review the stated tool and jurisdiction limits before use. Jurisdiction/provider scope: Compare a proposed send with an approved list of recipient roles and document IDs. Status: Proposed / not tested. The public discussion supports the problem; the method source supports only the documented features. No outcome from this adapted recipe has been verified. Verification: The linked sources support the complaint and documented method components. We have not run this recipe or verified its results. The example below is synthetic, not a customer result. ## The problem Compare a proposed send with an approved list of recipient roles and document IDs. Why it matters: A wrong recipient or attachment can expose information the firm did not intend to share. Checking an approved send manifest adds a review step, while the sender still verifies real addresses and file versions in the mail client. ## Sources and evidence - pain: [Pain evidence: Worst mistake at work discussion](https://www.reddit.com/r/paralegal/comments/1x17nzq/paralegals_whats_the_worst_mistake_youve_ever/) Worst mistake at work discussion, comments dated 2026-10-09, recent. A commenter recounts a colleague sending an internal strategy report to opposing counsel rather than the client; other comments describe accidental client inclusion. These are anecdotes in comments, not verified incident reports. - method: [Method: Outlook MailTips](https://support.microsoft.com/en-us/outlook/outlook-mailtips-options) Outlook MailTips provides recipient-related warnings in supported Exchange accounts. It does not validate legal permission or fully inspect every attachment; the manifest check below is a separate proposed control. Source checked: October 15, 2026. Pain reports are self-reported and identities are unverified. Method documentation supports components, not a tested end-to-end workflow. ## Suggested approach Start when: External message is ready for review 1. compare recipient roles and attachment IDs against an approved distribution manifest 2. Keep row or page references and mark missing or ambiguous evidence. Do not apply the suggested changes. 3. The responsible staff member checks the draft against the source records and approves any separate action. ## What you need - A selected high-risk unsent message, sender-approved exact distribution/attachment manifest and secure access to the actual recipient addresses and file versions. - Outlook MailTips is supplemental and requires a supported Exchange account; unavailable MailTips cannot be treated as an all-clear. - Existing firm-approved Acrobat Studio, AI Assistant add-on, or another plan including Acrobat AI; online services/cloud storage, language and region must be permitted. No purchase, login or connection is part of this verification. The manual route works without AI. - Preserve original evidence unchanged in restricted storage. Use synthetic material first. Prepare a separate, explicitly approved minimized AI input; aliases alone do not anonymize narrative or attachments. Do not upload raw originals or an alias key merely because another tab/file is sanitized. - Use synthetic inputs first. Keep real data in firm-approved accounts and processing, with appropriate access, confidentiality and retention controls. Aliases alone do not anonymize records. Never paste credentials, API keys or unnecessary client details. ## How to use Documentation-verified component path; proposed adaptation, not tested - Manually preparing metadata for every ordinary email may cost more than a careful checklist. Use selected consequential sends or an already maintained approved manifest. - No universal draft-recipient/attachment CSV export is verified. Role aliases are assigned by staff; actual address expansion, link access and attachment contents must be checked inside the secure mail client. Access and setup: - Actual account access, source versions/completeness, privacy approval and reviewer sign-off were not observed. ### 1. Inspect the actual unsent message Tool: Outlook desktop and sender-approved manifest Location: Open the saved draft; inspect To, Cc, Bcc and every attachment/link; read available MailTips Read the actual expanded recipient addresses in all recipient fields, including reply-all additions or groups. If a group cannot be completely resolved, block it. Open each proposed attachment from the draft securely and compare its exact version/matter to the approved manifest; inspect link targets/access through the approved system. Manually record recipient aliases/roles and attachment IDs without copying strategy content. Expected output: Observed proposed-send list and separate approved-send list, with exact secure source references. Next step: Create a minimized role/attachment-ID comparison input; keep real addresses, sensitive filenames and document content local. Check before continuing: MailTips warns about some recipient situations; it does not establish permission or attachment correctness. Changes to the draft invalidate the snapshot. Execution status: Official public documentation checked 2026-10-15; no account, source-data acquisition, prompt run or end-to-end workflow was tested. Step documentation: https://support.microsoft.com/en-us/outlook/outlook-mailtips-options https://support.microsoft.com/en-gb/outlook/mail/save-an-outlook-message-as-a-eml-file-a-pdf-file-or-as-a-draft ### 2. Load only the approved AI input Tool: Acrobat PDF Spaces Location: Acrobat homepage > PDF Spaces > Create a PDF Space > upload files or Paste copied text > Add to PDF Space Add the minimized approved-send, proposed-send and attachment-version/shareability records. Use clear source/version labels and verify the Files panel. Do not add originals that have not separately been cleared for Adobe processing. Expected output: Visible approved source set in the PDF Space; no account integration is implied. Next step: Use the AI Assistant message field in this same space for the next prompt. Check before continuing: Confirm every named source is actually loaded and readable. PDF Spaces supports up to 100 files, 100 MB and 600 pages per file; unsupported/password-protected/handwritten material blocks affected extraction. Execution status: Official public documentation checked 2026-10-15; no account, source-data acquisition, prompt run or end-to-end workflow was tested. Step documentation: https://helpx.adobe.com/acrobat/desktop/explore-pdf-spaces/create-pdf-spaces.html https://helpx.adobe.com/acrobat/desktop/explore-pdf-spaces/supported-formats-limitations.html https://helpx.adobe.com/acrobat/desktop/explore-pdf-spaces/pdf-spaces-faq.html ### 3. Run the bounded prompt and inspect citations Tool: Acrobat AI Assistant Location: The PDF Space AI Assistant message field Paste the prompt below. Open each source-number citation, check it, and use Copy to transfer the answer into a new local Word document or text file. Correct errors using the originals before reliance. Prompt: ```text Compare only the approved and proposed send manifests. Return message_id,matter_alias,recipient_role_or_attachment_id,exception,evidence_refs,required_review. Flag unexpected recipients, reply-all expansion, unknown group membership, internal-only attachments, wrong-matter IDs, wrong versions and missing approvals. Never infer consent or an alias-to-person mapping. Incomplete metadata means manual verification required. Do not inspect or repeat strategy content, change permissions, alter the draft or send anything. ``` Expected output: Recipient/attachment mismatches and approval blockers. Next step: Save the checked draft as send-check-review.docx; carry source IDs, versions and reviewer corrections into the next review step. Check before continuing: Human verifies the real exact addresses and actual attached files again immediately before any send; alias agreement alone is insufficient. Execution status: Official public documentation checked 2026-10-15; no account, source-data acquisition, prompt run or end-to-end workflow was tested. Step documentation: https://helpx.adobe.com/acrobat/desktop/use-acrobat-ai/generative-ai-features/ai-get-answers.html ### 4. Human review and final handoff Tool: Responsible staff reviewer and lawyer/process owner Location: Local reviewed report beside the frozen source set Sender checks the final draft’s exact To/Cc/Bcc addresses, recipient-group expansion, attachment bytes/version and any linked-file permissions against the approval. Resolve all blockers and record disposition. Expected output: Version-specific send checklist. Next step: Sending remains a separate authorized human action; this is not a confidentiality guarantee. Check before continuing: All unresolved or unreadable evidence stays open. No inferred approval or external action follows from AI output. Execution status: Official public documentation checked 2026-10-15; no account, source-data acquisition, prompt run or end-to-end workflow was tested. Step documentation: https://support.microsoft.com/en-us/outlook/outlook-mailtips-options ## What you will get send-review.csv: message_id, check, approved_value, proposed_value, attachment_id, finding, human_check_required. No live changes. ## Human review and limits Sender verifies exact real addresses, document versions and authorization inside the mail client. Test an opposing-counsel recipient substituted for client and a similarly named attachment from another matter. The assistant drafts or reports only. Check source records and review the output before a human performs any separately approved send or change. No automatic legal decision, money movement, account connection or publication is included. What to measure: During the pilot, count findings confirmed by the reviewer, false alarms, and missing-input cases. Do not infer time or money saved. ## Original prepared-input schema approved-send.csv: message_id, matter_alias, approved_recipient_role_ids, approved_attachment_ids. proposed-send.csv: message_id, matter_alias, proposed_recipient_role_ids, proposed_attachment_ids. attachments.csv: attachment_id, matter_alias, shareability_label, approved_version_id. Synthetic example input: ```text MSG1: CLIENT1 approved, OPPOSING_COUNSEL1 proposed MSG2: internal-only attachment proposed MSG3: approved IDs, exact real addresses not yet checked ``` Expected synthetic output: ```text MSG1: recipient mismatch MSG2: attachment blocker MSG3: sender still verifies real addresses and file versions ``` Failure check: Sender verifies exact real addresses, document versions and authorization inside the mail client. Test an opposing-counsel recipient substituted for client and a similarly named attachment from another matter. ## Starter files Native blank scaffolds and original synthetic examples may use different schemas. Follow NATIVE-INPUT-MAPPING where supplied. These files do not connect accounts or install automation. - [Download starter kit](https://agents.paretoid.com/assets/starter-kits/a22-starter-kit.zip) — All inputs, synthetic examples and review notes in one ZIP. No automation is installed. - [Start here: get the sources and prepare the review](https://agents.paretoid.com/assets/starter-kits/a22/START-HERE.txt) — Documentation-checked acquisition, explicit manual mapping, exact prompts and human review limits - [Setup and review checklist](https://agents.paretoid.com/assets/starter-kits/a22/README.txt) — Required inputs, file use, review steps and limits - [Approved send blank CSV](https://agents.paretoid.com/assets/starter-kits/a22/approved-send-template.csv) — Blank input headers for approved-send.csv - [Approved send synthetic example](https://agents.paretoid.com/assets/starter-kits/a22/approved-send-example.csv) — Synthetic test records for approved-send.csv - [Proposed send blank CSV](https://agents.paretoid.com/assets/starter-kits/a22/proposed-send-template.csv) — Blank input headers for proposed-send.csv - [Proposed send synthetic example](https://agents.paretoid.com/assets/starter-kits/a22/proposed-send-example.csv) — Synthetic test records for proposed-send.csv - [Attachments blank CSV](https://agents.paretoid.com/assets/starter-kits/a22/attachments-template.csv) — Blank input headers for attachments.csv - [Attachments synthetic example](https://agents.paretoid.com/assets/starter-kits/a22/attachments-example.csv) — Synthetic test records for attachments.csv - [Synthetic example expected results](https://agents.paretoid.com/assets/starter-kits/a22/expected-results.txt) — Compare a pilot result with the planted exceptions ## Optional original prepared-input prompt Destination: Your firm-approved AI assistant · prepared files This original prompt uses its own prepared-input schema. Do not mix it with native-step tables without the supplied mapping. ```text Compare this message's deidentified recipient roles and attachment IDs with the approved send manifest. Flag unexpected recipients, reply-all expansion, internal-only attachments, wrong-matter IDs and missing approval. Do not inspect or repeat strategy content, infer consent, change permissions or send. If metadata is incomplete, mark ‘manual verification required.’ INPUTS approved-send.csv: message_id, matter_alias, approved_recipient_role_ids, approved_attachment_ids. proposed-send.csv: message_id, matter_alias, proposed_recipient_role_ids, proposed_attachment_ids. attachments.csv: attachment_id, matter_alias, shareability_label, approved_version_id. OUTPUT send-review.csv: message_id, check, approved_value, proposed_value, attachment_id, finding, human_check_required Use only the supplied synthetic or firm-approved inputs. Cite source row or page IDs for each finding. Keep unknowns unresolved. Return a draft for the responsible staff reviewer. Do not send messages, connect accounts, change records, move money, or make legal decisions. Keep source files unchanged. If an input or permission is missing, list what is needed and stop that check. ``` Proposed / not tested · editorial prompt Published by Law Firm Agents. Proposed adaptation; not tested. Not legal advice.