Check that emails and attachments were filed

Practice relevance

Cross-practice idea · A general operational method. Review the stated tool and jurisdiction limits before use.

The problem

Compare the filing request list with actual message and attachment records.

Why it matters: Selecting an email for filing is not the same as confirming that the message and every attachment reached the right matter. A post-filing check makes delayed sync and missing records visible.

Sources & evidence

Proposed / not tested. The public source describes the problem. Documentation supports only the stated method components; no result from this recipe has been verified.

What’s been verified

Source methods and reported problems have been reviewed. We have not run the adapted workflow. The sample below describes expected behavior on synthetic data, not a customer result.

What to measure: In a synthetic pilot, count correctly found exceptions, false alarms, and unresolved inputs. No time or cost saving is assumed.

Pain evidence: Solution for saving and filing emails ↗Solution for saving and filing emails, 2020-07-06, older. A small-firm owner says dragging and renaming emails into OneDrive consumes substantial staff time; a practitioner describes cumbersome Outlook-to-practice-system filing. Clio Manage: save PDFs/docs, 2025-03-18, reports that losing a save button also removes a reminder to file documents. Direct open of the first thread failed; indexed original text was available.
Pain evidence: Clio Manage: save PDFs/docs ↗Additional self-reported public account; no independent identity or outcome verification.
Method: Clio Outlook Add-in ↗Clio Outlook Add-in, updated 2026-04-08, documents filing emails and attachments plus Not yet filed/Filed to Clio status. Sync is scheduled rather than instantaneous; shared inboxes are unsupported. The firm must verify its Outlook/Microsoft 365 eligibility.

Source checked: October 15, 2026. Pain accounts are self-reported. Documentation supports components; this adapted recipe and prompt have not been tested. We wrote these prompts. The adapted workflow hasn’t been tested.

Suggested approach

Start when: Day-end or post-filing check

compare the selected-for-filing register with actual communication and attachment records
Keep source references and report unknowns instead of filling gaps.
The responsible reviewer checks the report before any separately approved action.

Limits and review

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.

Who reviews it: Staff confirm original records inside the secure systems. Turn off unintended automatic time-entry behavior during an approved pilot. Test delayed sync and a thread where only one of two attachments was selected.

What you need

Your firm-approved AI assistant · prepared files

Existing authorized Clio Outlook add-in and Clio Manage access; selected-for-filing message/attachment list and approved matter mapping.
Clio documents Outlook 2016+ and Microsoft 365 Business on Microsoft-backed email; shared inboxes are unsupported. Do not install, reconnect or relax browser security for this recipe.
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

Before you start

A Filed to Clio tag can lag because synchronization is scheduled. A tag or File Email button is not proof that every message/attachment reached the correct matter.
The source and destination ID/attachment mapping is a manual check unless the firm already maintains it; there is no verified one-click complete reconciliation export.
A live filing step may also create time entries or move messages depending on existing settings; this review does not trigger filing or change settings.

Check access and setup

Actual account access, source versions/completeness, privacy approval and reviewer sign-off were not observed.

Inspect what was selected for filing
Outlook and existing Clio add-in · Open message > Clio icon > File Email panel > expand thread/attachment down arrow
Inspect the selected message/thread and individual attachments without pressing the final File Email action. Record original message/attachment identity, intended matter alias, visible status and capture time. Compare to the maintained selected-for-filing list; missing prior selection evidence stays unknown.
Expected output
Manually captured expected message/attachment inventory and add-in status.
Next step
Open actual Clio matter Communications and Documents, not merely the Outlook category.
Check before continuing
Do not activate Add a time entry or move-to-folder; these controls can have separate effects.
Step documentation 1 ↗
Verify receiving-side records
Clio Manage · Selected matter > Communications > Logs > Emails; matter > Documents
Open each claimed filed email and each expected attachment in the actual matter. Match content/version and provenance using permitted local identifiers, not just filenames or sender names. Record receiving record ID/locator, actual matter and capture time; if identity cannot be established, mark uncertain.
Expected output
Receiving-side communication/attachment evidence with source/destination mapping.
Next step
Prepare a separate alias-only selected-emails/filed-records ledger and scope note for AI review.
Check before continuing
Check every selected attachment separately. Pending scheduled sync stays pending; absent receiving evidence is not success.
Step documentation 1 ↗
Load only the approved AI input
Acrobat PDF Spaces · Acrobat homepage > PDF Spaces > Create a PDF Space > upload files or Paste copied text > Add to PDF Space
Add the minimized selected-email/attachment inventory, receiving-side ledger and scope/status policy. 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.
Step documentation 1 ↗Step documentation 2 ↗Step documentation 3 ↗
Run the bounded prompt and inspect citations
Acrobat AI Assistant · 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.
Acrobat AI Assistant promptCompare these observed selected-email and receiving-side filing ledgers using only verified message/attachment mappings. Return source_message_id,attachment_id if applicable,intended_matter,observed_matter,receiving_ref,status,exception,evidence_refs. Flag missing attachments, wrong matters, duplicates and unverifiable identities. Treat Not yet filed or delayed sync as pending, never success. A Filed to Clio tag alone cannot satisfy receiving-side evidence. Do not infer matters from names, refile, create time entries, move/delete originals or forward anything.
Expected output
Source-linked filing exceptions and unresolved identity/sync states.
Next step
Save the checked draft as email-filing-review.docx; carry source IDs, versions and reviewer corrections into the next review step.
Check before continuing
Staff verifies all receiving records, not just an add-in tag. Any later attachment/version change invalidates the old check.
Step documentation 1 ↗
Human review and final handoff
Final human review
Responsible staff reviewer and lawyer/process owner · Local reviewed report beside the frozen source set
Staff checks pending sync again through the actual receiving records under the firm’s normal process; confirmed missing/wrong-matter findings go to an authorized correction owner.
Expected output
Reviewed message-and-attachment filing evidence register.
Next step
Refiling, time-entry creation, deletion or corrective communications require separate authorization.
Check before continuing
All unresolved or unreadable evidence stays open. No inferred approval or external action follows from AI output.
Step documentation 1 ↗

What you’ll get

filing-review.csv: message_id, approved_matter_alias, observed_matter_alias, status, missing_attachment_ids, evidence_rows

Inputs and a sample test Synthetic example · not a measured result

Input files

selected-emails.csv: message_id, approved_matter_alias, expected_attachment_ids, selection_time
filed-records.csv: message_id, matter_alias, attachment_id, filing_status, observed_at; scope.txt: approved sync interval and export cutoff

Synthetic example

M1: Not yet filed status
M2: message filed with one of two expected attachments
M3: message filed to a different matter

Expected output

M1: pending, not success
M2: missing-attachment exception
M3: wrong-matter review

Test a failure

Staff confirm original records inside the secure systems. Turn off unintended automatic time-entry behavior during an approved pilot. Test delayed sync and a thread where only one of two attachments was selected.

Try with the sample files

Follow the tool steps above and use the inputs named in each step. Where provided, native-* files are blank scaffolds and NATIVE-INPUT-MAPPING explains their fields. Original examples and the optional full review prompt use a separate prepared-input schema. Keep them separate unless the mapping explicitly connects them. Downloading a kit does not connect accounts or prove the workflow works.

Download inputs and checklist 10 files

Instructions, blank templates and separate synthetic examples; these files do not install an automation. Blank templates still need verified source data.

Download starter kit All inputs, synthetic examples and review notes in one ZIP. No automation is installed.
Start here: get the sources and prepare the review Documentation-checked acquisition, explicit manual mapping, exact prompts and human review limits
selected-emails.csv Blank input template with exact recipe headers.
selected-emails.example.csv Separate synthetic fixture input. Do not mix these rows into real exports.
filed-records.csv Blank input template with exact recipe headers.
filed-records.example.csv Separate synthetic fixture input. Do not mix these rows into real exports.
scope.txt Blank text input worksheet. Fill its fields with approved evidence; no default assumptions are supplied.
scope.example.txt Separate synthetic text input fixture; use with the example CSV files only.
Expected fixture findings Read-only expected output and failure conditions for the included synthetic input files.
Setup and review checklist Recipe-specific prerequisites, file mapping, prompt, setup steps, checklist and limits.

Optional full review prompt for prepared inputs

Prepared-input review prompt with Your firm-approved AI assistant · prepared files

Compare these deidentified selected-email and filed-record manifests. Verify matter ID, message ID and expected attachment IDs. Treat ‘Not yet filed’ as pending, never success. Flag missing attachments, mismatches and duplicates with source rows. Do not infer a matter from a name, refile, create time entries, delete originals or forward mail. Return an exceptions queue for staff.

INPUTS
selected-emails.csv: message_id, approved_matter_alias, expected_attachment_ids, selection_time
filed-records.csv: message_id, matter_alias, attachment_id, filing_status, observed_at; scope.txt: approved sync interval and export cutoff

OUTPUT
filing-review.csv: message_id, approved_matter_alias, observed_matter_alias, status, missing_attachment_ids, evidence_rows

Use only these synthetic or firm-approved inputs and preserve source row/page IDs. Keep missing or conflicting evidence unresolved. Return a draft for the named reviewer. Do not send messages, connect accounts, change records or permissions, move money, or make legal decisions. Keep source files unchanged. List missing prerequisites before continuing.

Proposed / not tested · editorial prompt. This prompt uses the original prepared-input schema shown in the sample test. Step prompts may use different tables. Follow NATIVE-INPUT-MAPPING where supplied; do not mix the original examples with native-step inputs without mapping and checking every field.

Read original method Read pain evidence