Skip to content
English
Contact us
  • There are no suggestions because the search field is empty.

Add Multiple Attachments to Email Without .ZIP

Date: 7/8/2025

Version: 0.2 (Discovery Phase)

Contributors: @Douglas Erickson (Deactivated)

https://cxtsoftware.atlassian.net/browse/XD-50254Pending approval

The Problem & Our Current Understanding

For customers who need to send multiple documents via email, they are unable to ensure delivery to recipients whose organizations block .zip files, which is critical now because it causes failed communications and requires inefficient manual workarounds.

Evidence: This issue was raised directly by customers and confirmed by our support team. The current system automatically compresses multiple attachments into a single .zip file, which is a common target for security filters. The cost of inaction is continued customer frustration, wasted time for our users, and a perception that our product cannot handle basic business communication needs, potentially impacting customer retention.

Target Users & Context

Primary Persona Profile: An Operations Coordinator or Accounts Receivable Clerk. This user works in a fast-paced office environment and is responsible for sending time-sensitive documents (invoices, reports, order confirmations) from our application. They use a standard desktop web browser. Their primary measure of success is efficiency and reliability – did the document get sent correctly and quickly?

Jobs-to-be-Done (JTBD): When I need to send multiple documents like an invoice PDF and its source CSV to a client, I want to attach them all to a single email and send them in a format they can receive, so that I can complete my task efficiently and ensure they get the information they need without issue.

Current Pains & Impact:

  • Pain: Emails with critical attachments are being rejected or quarantined without notification.

    • Quote: "My client's security blocks zip files, so I have to send the invoice PDF and the CSV data in two separate emails. It's confusing for them and a waste of my time."

    • Impact: Wasted time troubleshooting and resending documents; potential for delayed payments if invoices are not received promptly; appears unprofessional to the end-client.

Current Workarounds: Users are forced to send the email to an address that can open and uncompress the files, then have to manually resend the uncompressed files, to bypass the .zip compression. This is inefficient, increases work time, and increases the risk of manual error.

Secondary Stakeholders:

  • The End Recipient (Customer's Customer): Cares about receiving documents cleanly and easily without security warnings.

  • Internal Support Team: Cares about reducing the volume of support tickets related to blocked emails.

  • Recipient's IT/Security Department: Cares about maintaining their security posture, which is the root cause of the constraint.

Key Objectives & Success Metrics

  • Objective 1: Improve the deliverability and reliability of multi-document emails.

    • KR1: Achieve a ≥75% decrease in support tickets mentioning "blocked zip file" within six months post-launch. (Lagging)

    • KR2: Receive positive confirmation from the initial reporting customers that the solution resolves their issue. (Leading)

  • Objective 2: Enhance user satisfaction by providing a flexible email experience.

    • KR1: Achieve a feature adoption rate of ≥15% among users who send multiple attachments within the first quarter. (Leading)

    • KR2: See a measurable increase in CSAT scores for users who interact with the email feature. (Lagging)

    • Instrumentation Plan: We need to ensure we can track the usage of this new toggle option in our analytics platform (e.g., Pendo, Amplitude).

Hypotheses & Assumptions

Opportunity Hypothesis: We believe that by providing a simple, user-controlled option to send multiple attachments as individual files, we will empower users to bypass recipient zip filters. This will result in fewer support tickets, increased user satisfaction, and improved workflow efficiency.

Key Risks & Assumptions:

  • Adoption Risk: Users might not notice the new option or understand when to use it.

    • Mitigation: Design the feature to be clearly visible and understandable in the email workflow. Provide a tooltip or brief help text.

  • Technical Risk: Sending many large individual attachments might hit email server size limits (e.g., >25MB) more often than a single compressed file.

    • Mitigation Spike: Investigate typical file sizes and numbers of attachments. Consider adding a client-side warning if the total attachment size exceeds a certain threshold.

  • Scope Creep Risk: Users might request more complex logic (e.g., "zip only if more than 3 files").

    • Mitigation: Keep the MVP focused on a simple on/off toggle. Defer more complex rules to a future iteration based on feedback and data.

Discovery Partners & Interested Customers

  • Primary Discovery Partner: The customer who originally reported the problem. (Status: To be contacted for initial interviews and prototype feedback).

  • Secondary Discovery Group: A list of 3-5 other customers who have reported similar issues, to be provided by the Customer Support team. (Status: Awaiting list from Support).

Validation Plan (Next 4-6 Weeks)

(Timeline: July 8, 2025 – August 19, 2025)

Goal: Validate that a simple toggle to disable zipping is a sufficient and desirable solution for users who face this problem, and de-risk our technical approach.

Activities:

  1. User Interviews: Conduct interviews with the primary discovery partner and 3-5 other affected users to deeply understand the problem, frequency, and impact. (Owner: Product Manager, ETA: July 22, 2025)

  2. Prototype & Test: Create a low-fidelity mockup of the email screen with the proposed toggle/checkbox and conduct usability testing sessions to gauge discoverability and clarity. (Owner: UX Designer, ETA: Aug 5, 2025)

  3. Technical Spike: Investigate potential email server attachment size/count limits and research best practices for sending multiple attachments. (Owner: Lead Engineer, ETA: Aug 12, 2025)

Key Questions to Answer:

  • How widespread is this problem among our user base?

  • Is a simple on/off toggle the right level of control, or do users need more complex rules?

  • Where on the email screen is the most intuitive place for this new option?

  • What are the technical limitations (e.g., total attachment size) we need to design around?

  • What should the default behavior be (zip on vs. zip off)?