Check email recipients and attachments Get the source data and prepare the review Documentation-verified component path; proposed adaptation, not tested WHAT WAS CHECKED Official public documentation checked 2026-10-15; no account, source-data acquisition, prompt run or end-to-end workflow was tested. Menus/features are vendor-documented; prompts, field maps and human gates are editorial adaptations. No actual client work, account login, installation, connection, external write or site edit occurred. BEFORE YOU START - 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. DATA ACQUISITION LIMITS - 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. WHEN THIS CAN RUN Blocked until actual sources, permissions and required human approvals are supplied; no real inputs were available in this verification. STEP 1: Inspect the actual unsent message Tool: Outlook desktop and sender-approved manifest Open: Open the saved draft; inspect To, Cc, Bcc and every attachment/link; read available MailTips Access needed: See recipe prerequisites; exact account entitlement and permissions not observed. 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. Use it next: Create a minimized role/attachment-ID comparison input; keep real addresses, sensitive filenames and document content local. Check: MailTips warns about some recipient situations; it does not establish permission or attachment correctness. Changes to the draft invalidate the snapshot. Documentation limit: Sources support named component capabilities. Capture fields, prompts and review requirements are the proposed adaptation, not promised native export columns. Source 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 STEP 2: Load only the approved AI input Tool: Acrobat PDF Spaces Open: Acrobat homepage > PDF Spaces > Create a PDF Space > upload files or Paste copied text > Add to PDF Space Access needed: See recipe prerequisites; exact account entitlement and permissions not observed. 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. Use it next: Use the AI Assistant message field in this same space for the next prompt. Check: 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. Documentation limit: Sources support named component capabilities. Capture fields, prompts and review requirements are the proposed adaptation, not promised native export columns. Source 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 STEP 3: Run the bounded prompt and inspect citations Tool: Acrobat AI Assistant Open: The PDF Space AI Assistant message field Access needed: See recipe prerequisites; exact account entitlement and permissions not observed. 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. PASTE THIS PROMPT 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. Use it next: Save the checked draft as send-check-review.docx; carry source IDs, versions and reviewer corrections into the next review step. Check: Human verifies the real exact addresses and actual attached files again immediately before any send; alias agreement alone is insufficient. Documentation limit: Sources support named component capabilities. Capture fields, prompts and review requirements are the proposed adaptation, not promised native export columns. Source documentation: https://helpx.adobe.com/acrobat/desktop/use-acrobat-ai/generative-ai-features/ai-get-answers.html STEP 4: Human review and final handoff Tool: Responsible staff reviewer and lawyer/process owner Open: Local reviewed report beside the frozen source set Access needed: See recipe prerequisites; exact account entitlement and permissions not observed. 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. Use it next: Sending remains a separate authorized human action; this is not a confidentiality guarantee. Check: All unresolved or unreadable evidence stays open. No inferred approval or external action follows from AI output. Documentation limit: Sources support named component capabilities. Capture fields, prompts and review requirements are the proposed adaptation, not promised native export columns. Source documentation: https://support.microsoft.com/en-us/outlook/outlook-mailtips-options ACCOUNT AND SOURCE CHECKS STILL NEEDED - Actual account access, source versions/completeness, privacy approval and reviewer sign-off were not observed. USING THE FILES IN THIS KIT Use the exact files or source text named in the steps above. Native exports keep their own headers. The kit tables are editorial review worksheets; they are not a claim that a product exports those fields. Some routes use reviewed text directly or require additional original files. Never rename an unreviewed raw export to make it appear mapped. Keep expected-result files separate from inputs. The source account, actual data, prompts and end-to-end workflow were not tested. Any final communication, filing, permission change, payment or publication needs its own authorized human action. This guide performs none.