How to Handle Failed PDF Email Deliveries

Troubleshoot PDF email delivery failures by identifying the cause, validating recipients and attachments, retrying safely and retaining delivery records.

Contents
  1. How XERIA Email Distribution Fits the Workflow
  2. Step 2: Generate and Verify the Personalized PDFs
  3. Step 1: Review Mail Log
  4. Step 2: Review Failed Sends
  5. Step 3: Validate the Attachment
  6. Step 4: Run a Test Delivery
  7. Step 5: Start the Email Operation
  8. Step 6: Export or Retain Delivery Records
  9. Step 7: Handle Password-Protected PDFs Carefully
  10. Common Problems
  11. Recipient Email Is Empty
  12. Gmail Is Not Connected
  13. Microsoft Graph Token Is Missing
  14. Attachment File Is Not Found
  15. Attachment Appears Empty
  16. Send E-mail Only Cannot Find the PDF
  17. Subject Template Is Empty
  18. Body Template Is Empty
  19. The Wrong PDF Is Attached
  20. Some Recipients Received the Email and Others Failed
  21. The Email Was Sent but the Recipient Cannot Open the PDF
  22. Best Practices
  23. Frequently Asked Questions
  24. How Do I Know Which Emails Failed?
  25. Can I Resend Only Failed Recipients?
  26. Is Email Sending Available in Trial Mode?
  27. Conclusion

XERIA can distribute recipient-specific PDF files directly from the application by combining recipient records, reusable email templates, configured sending profiles and verified attachment mappings. This allows a personalized PDF workflow to continue from document generation into controlled email delivery without manually matching every file to every recipient.

How XERIA Email Distribution Fits the Workflow

Personalized email delivery normally follows document preparation and verification.

The most important relationship is not simply recipient-to-email. It is:

  • Recipient
  • Email address
  • Personalized PDF
  • Output filename or `PDF_PATH`
  • Email template
  • Sending profile
  • Delivery result

Every item must stay aligned.

  • A verified recipient list in XERIA
  • A valid email address for every intended recipient
  • The personalized PDF files
  • A configured mail-sending profile
  • An approved email subject
  • An approved email body
  • Any required email signature
  • The correct output folder or `PDF_PATH` values
  • A small group of test recipients
  • A process for reviewing Mail Log results

Generate and review high-risk documents before email delivery.

Do not begin with the full recipient list if the email profile, attachment mapping or template has not yet been tested.

The email address is essential for delivery.

Check for:

  • Empty email addresses
  • Misspelled addresses
  • Duplicate recipients
  • Test recipients
  • Shifted imported rows
  • Old addresses
  • Shared mailboxes used unintentionally
  • Recipient records linked to the wrong output file

XERIA reports an error when a recipient email is empty, but valid syntax alone does not prove that the address belongs to the intended person.

Step 2: Generate and Verify the Personalized PDFs

For sensitive workflows, generate the PDFs before sending them.

Use the personalized production workflow to:

  • Select the approved source PDF
  • Apply recipient-specific watermark data
  • Add trace information where required
  • Apply PDF security settings
  • Generate a separate file for each selected recipient
  • Review the output set

Before moving to email delivery, compare:

  • Selected recipient count
  • Generated file count
  • Output filenames
  • Recipient watermarks
  • Trace codes
  • Password assignments
  • Permission profiles

Open representative files and confirm that the intended recipient is visible or otherwise identifiable.

If the organization uses more than one sender account, give profiles clear names so the correct account can be identified before delivery.

A slower profile can be appropriate when provider limits, anti-abuse controls or operational caution matter more than throughput.

A faster profile may reduce total delivery time, but email providers can apply their own rate limits and security controls.

Do not assume that the highest sending speed is appropriate for every account.

Step 1: Review Mail Log

After sending, open **Mail Log**.

The log can include fields such as:

Mail Log Field Purpose
SentAt (UTC) Records the send time
Email Identifies the destination address
Name Identifies the recipient record
Subject Shows the generated subject
Status Shows the operation result
Error Records a send error where available
Attachment name Identifies the file sent
Attachment path Shows the file location used for the send

Use Mail Log to identify:

  • Successful sends
  • Failed sends
  • Recipient errors
  • Attachment errors
  • Provider errors
  • Items that need another attempt

Date filters are entered in local time and are converted for UTC-based queries.

Step 2: Review Failed Sends

Do not automatically resend every failure without examining the cause.

Typical failure categories include:

  • Recipient email is empty
  • Attachment file is missing
  • Attachment is invalid
  • Gmail is not connected
  • Microsoft Graph token is unavailable
  • Provider rejected the request
  • Subject template is empty
  • Body template is empty
  • Output path is wrong

Correct the root cause before retrying.

If only a subset failed, resend only the affected recipients where practical.

Use **Send E-mail Only** when the approved personalized PDFs already exist.

Step 3: Validate the Attachment

Before sending, XERIA checks the attachment.

Problems can include:

  • Attachment not found
  • Invalid path
  • File that appears too small or empty
  • Temporary PDF not created
  • Incorrect output folder
  • Expected filename not present

Treat attachment validation errors as a reason to stop the recipient’s send attempt.

Do not substitute a different file manually without updating the recipient mapping.

For a personalized workflow, the correct attachment is part of the recipient’s security context.

Step 4: Run a Test Delivery

Select a small test group before sending the full batch.

The group should include:

  • A standard recipient
  • A recipient with a long name
  • A non-Latin recipient name
  • A protected PDF
  • A large but normal attachment
  • A recipient using a different mail domain
  • A record using `PDF_PATH`, if that feature will be used

Use test addresses controlled by the organization where possible.

Verify the received email:

  • Sender identity
  • Recipient address
  • Subject
  • Body
  • Signature
  • Attachment filename
  • Attachment contents
  • Password behavior
  • Watermark
  • Trace information

Confirm that the received attachment is the intended recipient’s document.

Step 5: Start the Email Operation

After successful testing, select the approved recipients and begin the email operation.

Monitor:

  • Current recipient
  • Completed sends
  • Failed sends
  • Skipped recipients
  • Authentication errors
  • Attachment errors
  • Provider errors
  • Missing recipient addresses

Do not treat a completed operation as proof that every recipient successfully received the email.

A send attempt may fail for reasons outside XERIA, including provider or account restrictions.

Step 6: Export or Retain Delivery Records

Mail Log can support operational review and record retention.

Where required, retain:

  • Recipient
  • Email address
  • Send timestamp
  • Subject
  • Status
  • Error information
  • Attachment name
  • Attachment path

XERIA includes options associated with exporting Mail Log data to CSV or Excel.

Protect exported logs because they can contain recipient and document-distribution information.

Apply the organization’s retention policy rather than keeping delivery data indefinitely.

Step 7: Handle Password-Protected PDFs Carefully

If the attached PDF requires an open password, the password-delivery process should remain separate where required by policy.

Before sending the PDF:

  • Confirm the correct password is assigned
  • Confirm the recipient identity
  • Confirm the attachment is correct
  • Confirm the email address
  • Confirm how the password will be delivered
  • Keep plaintext passwords out of ordinary Mail Log records
  • Do not place passwords in filenames

Common Problems

Recipient Email Is Empty

Correct the recipient record before sending.

Do not replace the destination with another address unless that address is verified for the same recipient.

Gmail Is Not Connected

Connect the Gmail account through **Settings > Mail Management** and test the profile before restarting the production send.

Microsoft Graph Token Is Missing

Re-establish the required Microsoft 365 authentication state before retrying the send.

Attachment File Is Not Found

Check `PDF_PATH`, output folder and expected filename.

Confirm the file was not moved, renamed or deleted.

Attachment Appears Empty

Open the PDF manually and verify that it is a valid generated document before retrying.

Send E-mail Only Cannot Find the PDF

Fill `PDF_PATH` with the full file path or select the correct output folder containing the expected PDF.

Subject Template Is Empty

Select or create a valid email template and provide an approved subject.

Body Template Is Empty

Add the approved email message before sending.

The Wrong PDF Is Attached

Stop the batch.

Review recipient records, output filenames, `PDF_PATH` values and attachment mappings.

Do not continue sending until the mapping is corrected.

Some Recipients Received the Email and Others Failed

Review Mail Log and isolate the failed records.

Correct the specific cause and resend only the affected recipients where appropriate.

The Email Was Sent but the Recipient Cannot Open the PDF

Verify that the recipient received the correct password through the approved password-delivery method and that the attachment itself is the intended file.

Best Practices

  • Verify the recipient list before every send.
  • Generate and review sensitive PDFs before emailing them.
  • Keep recipient-to-file mappings explicit.
  • Use unique, collision-resistant filenames.
  • Configure mail profiles before production day.
  • Test provider authentication.
  • Use reusable approved email templates.
  • Preview dynamic recipient content.
  • Keep subjects concise.
  • Avoid sensitive data in subject lines.
  • Keep PDF passwords separate from protected attachments where required.
  • Use an appropriate sending-speed profile.
  • Test a small recipient group first.
  • Validate attachments before sending.
  • Use `PDF_PATH` carefully.
  • Use **Send E-mail Only** for already approved files.
  • Monitor provider and attachment errors.
  • Review Mail Log after every batch.
  • Retry only failed recipients where practical.
  • Protect Mail Log exports.
  • Reconcile selected recipients, attachments and send results.
  • Combine delivery records with watermark and trace evidence.
  • Stop immediately when the wrong attachment is detected.

Frequently Asked Questions

How Do I Know Which Emails Failed?

Review **Mail Log**. It records delivery status and can include error, recipient, subject and attachment information.

Can I Resend Only Failed Recipients?

When the approved PDFs already exist, use the existing recipient records and **Send E-mail Only** for the recipients that need another attempt.

Is Email Sending Available in Trial Mode?

No. Email delivery requires the relevant licensed functionality and is unavailable in trial mode.

Conclusion

XERIA can extend a personalized PDF workflow from document creation to recipient-specific email delivery.

The reliable sequence is to verify recipient data, generate and inspect the personalized PDFs, configure the sender profile, prepare an approved reusable template, confirm every recipient-to-attachment mapping, run a small test and then send the production batch.

After delivery, Mail Log provides the operational record needed to identify successes and failures. When approved PDFs already exist, **Send E-mail Only** allows them to be delivered without regenerating the documents.

The most important control remains the recipient-to-file relationship: the right PDF, sent to the right email address, through the right profile, with the right security and traceability settings.

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