Digital receipts are easiest to manage when every file is connected to the expense it supports—not buried in an email inbox or a generic folder. A workable system needs four things: a readable image or PDF, a clear transaction record, the correct Business, and a routine for resolving anything incomplete.

Start at the moment of purchase

Save the receipt as soon as possible. Email receipts can be downloaded as PDFs; paper receipts can be photographed or scanned. Before filing, confirm that the supplier, date, amount and purchased items are readable. If the image is blurred or cut off, capture it again while the original is available.

Use a predictable filename such as YYYY-MM-DD_supplier_amount. The filename is only a finding aid—the expense record should still hold the date, amount, payment source and business purpose.

Connect evidence to one expense

A receipt, card transaction and email confirmation may all describe the same purchase. Treat them as evidence for one event instead of creating three expenses. Match using several facts together:

• transaction date;
• supplier;
• total and currency;
• payment method or account; and
• the Business that incurred the cost.

If something does not agree, leave a review note rather than changing a value to force a match.

Keep each Business separate

When you operate more than one Business, choose the Business before attaching the receipt. Avoid a shared “business receipts” folder with no ownership context. The CRA advises keeping separate records for each business you run.

In SilaTrail, attach the receipt to the expense in the selected Business. Then use monthly review to find missing evidence and unresolved records.

Use a simple weekly routine

Once a week:

1. import emailed and photographed receipts;

2. check image readability;

3. match each document to an existing expense before creating a new one;

4. add a plain-language purpose;

5. confirm the Business and payment source; and

6. flag exceptions for follow-up.

This small routine prevents a large cleanup at month-end.

Back up what matters

Electronic records must remain accessible and readable. Keep recoverable backups and periodically test that files open. Do not assume a phone gallery or email provider is a complete records system.

Frequently asked questions

Should I keep the original filename from the supplier?

You may keep it, but a consistent local filename can make retrieval easier. The record itself should carry the authoritative transaction details.

Can I throw away a paper receipt after scanning it?

Do not assume every scan permits immediate destruction of the paper original. Review the CRA’s imaging requirements and get professional advice for unusual or high-value documents.

How long should I keep receipts?

The general CRA rule is six years from the end of the last tax year the records relate to, but exceptions exist. Confirm the rule that applies to your situation.

Official guidance

Review the CRA’s Keeping records, acceptable formats and backups, and business records.

This article explains record organization, not tax deductibility or accounting treatment.