How to Check Email Delivery and Track Sent Secure Messages

Applies to: Microsoft 365, Outlook, Google Workspace, Gmail, and Organizations Using TSN Cyber Email Security
Difficulty: Beginner
Estimated Time: 5–10 minutes

Overview

TSN Cyber Email Security uses Trustifi technology to help protect outgoing business emails and provide information about email delivery and recipient activity.

Depending on your organization’s configuration, you may be able to determine whether a message was delivered, opened, or accessed through a secure email portal.

Tracking is especially useful when sending:

  • Confidential business documents.
  • Secure encrypted messages.
  • Important contracts.
  • Customer correspondence.
  • Time-sensitive business information.
  • Approved financial documents.

This guide explains how to check sent messages, understand delivery and tracking information, and troubleshoot emails that appear to be missing or undelivered.

Before You Begin:

  • Have access to your organization’s approved email account.
  • Confirm that the message was sent from your work email address.
  • Know the recipient’s email address.
  • Have the approximate sending date and time available.
  • Use the approved TSN Cyber or Trustifi interface if tracking access is enabled.

Important: Not every email or account has recipient tracking enabled. Your organization controls which tracking features are available.

Note: A message showing as Delivered does not necessarily mean that the recipient opened, read, or understood it.

Understanding Email Delivery vs. Email Tracking

Email delivery and email tracking are two different things.

Email Delivery

Delivery information helps determine whether an email was successfully accepted by the relevant mail delivery system.

Email Tracking

Tracking information may help determine whether certain recipient actions occurred, such as:

  • Opening the message.
  • Accessing encrypted content.
  • Clicking a tracked link.
  • Downloading a protected attachment.

These events are available only when supported and enabled.

What’s the Difference?

StatusWhat It Generally Means
SentYour email application submitted the message
DeliveredThe relevant delivery system accepted the email
OpenedA message-opening event was detected
Link ClickedA tracked link was accessed
Attachment DownloadedA protected attachment download was recorded
FailedDelivery was unsuccessful
QuarantinedA security policy held or blocked the message

Important: Delivery and activity tracking are not proof that a particular person read the message. Automated security scanners can generate tracking events.

Step 1: Check Your Sent Items Folder

Before investigating delivery, confirm that the message was actually sent.

Microsoft Outlook

  1. Open Microsoft Outlook.
  2. Select your work mailbox.
  3. Open Sent Items.
  4. Locate the message.
  5. Confirm the recipient’s email address.
  6. Review the date and time.

If the message is missing, check Drafts and Outbox where available.

Gmail

  1. Open Gmail.
  2. Select Sent from the navigation menu.
  3. Locate the message.
  4. Confirm the recipient.
  5. Review the date and time.

If the message is not listed, check Drafts and any displayed sending errors.

Important: A message appearing in Sent Items only confirms that your email application recorded it as sent. It does not independently prove final delivery to the recipient.

Step 2: Check for a Delivery Failure Notification

If an email cannot be delivered, you may receive a notification describing the problem.

These messages are sometimes called:

  • Non-Delivery Reports.
  • Bounce Messages.
  • Delivery Failure Notifications.

Locate a Failure Message

  1. Open your Inbox.
  2. Search for a delivery failure notification.
  3. Review the recipient address.
  4. Read the error message.
  5. Identify which original email failed.

Common causes include:

  • Incorrect recipient address.
  • Recipient mailbox unavailable.
  • Recipient mail server rejection.
  • Security policy restrictions.
  • Other temporary or permanent delivery failures.

Important: Do not repeatedly resend confidential emails without first checking why delivery failed.

Step 3: Review Your Trustifi Account

If your organization provides sender access to Trustifi tracking:

  1. Open your organization-approved Trustifi portal.
  2. Sign in using your assigned work account.
  3. Complete any required authentication.
  4. Look for your sent messages or an available tracking area.
  5. Select the message you want to review.

Depending on your permissions and enabled features, you may see outbound message activity.

Note: Trustifi’s administrative email trace interface is separate from the ordinary user experience. You may not have access to detailed delivery logs.

If you cannot find tracking information, contact True Synergy Networks.

Step 4: Find the Sent Email

If your account provides a sent-message history:

  1. Open the available message list.
  2. Search for the recipient’s email address.
  3. Review the subject.
  4. Confirm the date and time.
  5. Select the intended message.

Tip: When reporting a delivery issue, include the recipient, subject, and approximate sending time so TSN can locate the correct message.

Important: Avoid opening or sharing sensitive message content with people who are not authorized to view it.

Understanding Trustifi Delivery Status

Trustifi’s outbound delivery tracing supports several status indicators.

Delivered

The email was successfully handed off according to the applicable mail delivery process.

Important: Delivery does not guarantee the message appeared in the recipient’s Inbox. The receiving service may apply additional filtering.

Quarantined

A security rule or policy prevented the message from being delivered normally.

The message may require authorized review.

In Process

Trustifi is still processing the message.

If the status does not change after a reasonable period, contact True Synergy Networks.

Failed

Delivery failed because of an error, such as an invalid recipient or a receiving server rejection.

Note: Trustifi’s detailed delivery indicators and underlying tracking depend on the organization’s mail routing architecture. Some configurations cannot report final delivery through Trustifi itself.

Step 5: Understand Open Tracking

When enabled, Trustifi may record when an email is opened or its protected content is accessed.

Example

You send a secure message to a customer.

The customer opens the message through the secure portal.

Trustifi may record the opening event.

Depending on your organization’s policies, you may receive a notification.

Important: An Opened status does not necessarily prove that the intended human recipient read the email.

Some mail systems use automated security scanners that can open messages or inspect links.

Other email clients may prevent tracking information from being collected.

Understanding Automated Security Scanning

Some recipient mail systems automatically inspect incoming messages.

These systems may:

  • Open messages in a controlled environment.
  • Follow links for security analysis.
  • Inspect attachments.
  • Generate events that resemble ordinary recipient activity.

Trustifi may identify some activity as an automated audit rather than a normal human opening.

Example

You send an email and receive a notification that it was opened almost immediately.

This may represent automated security inspection rather than the recipient personally reading the message.

Important: Do not assume a recipient is available or has read an email based solely on an opening notification.

Step 6: Understand Link Tracking

If your organization enables link tracking, Trustifi may record when links in outgoing messages are accessed.

What You May See

Depending on configuration:

  • A link interaction event.
  • The date and time.
  • Related message information.

Important Limitations

Link tracking cannot always distinguish between:

  • A real person clicking a link.
  • Automated mail security analysis.
  • Other supported security or preview processes.

Important: Do not use a link-click event as definitive evidence that the recipient personally visited the linked website.

Step 7: Understand Attachment Download Tracking

Trustifi can support notifications when recipients download protected attachments.

Example

You send a confidential PDF through a Trustifi encrypted email.

The recipient opens the secure message and downloads the attachment.

If the appropriate tracking feature is enabled, the activity may be recorded.

What Download Tracking Means

A recorded download indicates that the secure delivery system detected a download action.

It does not prove:

  • The document was read.
  • The document was reviewed completely.
  • The recipient accepted its contents.
  • The file was not downloaded by an automated or delegated process.

Important: For documents requiring formal acceptance or signatures, use an approved electronic signature or document acknowledgment process.

Step 8: Check Whether the Recipient Received the Message

If tracking is unavailable or unclear, use a direct confirmation.

Confirm the Address

  1. Open your Sent Items folder.
  2. Locate the original email.
  3. Verify the recipient’s email address.
  4. Check for spelling errors.

Ask the Recipient to Check Their Mailbox

Using a trusted communication method, ask the recipient to review:

  • Inbox.
  • Junk or Spam.
  • Other or filtered mail folders.
  • Their organization’s quarantine, if accessible.

Important: Do not ask a recipient to disable their email security protections to receive your message.

Step 9: Verify a Secure Encrypted Email

If you sent the message using Trustifi encryption, the recipient may receive a notification containing a secure viewing link.

Confirm the Recipient’s Experience

Ask whether they:

  1. Received the secure notification.
  2. Opened the approved secure message link.
  3. Completed the required authentication.
  4. Accessed the message content.
  5. Were able to view any intended attachments.

If the recipient cannot access the message, ask for the displayed error, without requesting any passwords or authentication codes.

Important: Receiving a secure message notification is different from successfully accessing the encrypted contents.

Step 10: Understand Secure Message Expiration

Some Trustifi encrypted emails have an expiration period.

After the expiration:

  • The secure viewing link may no longer work.
  • Protected attachments may be inaccessible.
  • The recipient may need a newly sent message.

If the Message Has Expired

  1. Verify that the original message is no longer accessible.
  2. Confirm whether the recipient still needs it.
  3. Send a replacement secure message if authorized.
  4. Apply your organization’s required security settings.

Important: Expiration does not remove copies previously downloaded or retained by a recipient.

Step 11: Understand Recipient Blocking

Certain Trustifi encrypted email configurations allow a sender to restrict future recipient access.

For example, an authorized sender may be able to block:

  • Further access to encrypted message content.
  • Additional downloads of protected attachments.

Important: Blocking a recipient does not guarantee that previously viewed, copied, or downloaded information can be removed.

If you sent sensitive information to the wrong person, contact True Synergy Networks immediately.

Step 12: Understand Message Tracking Notifications

Your organization may enable automatic notifications for certain email events.

Examples include:

  • A message was opened.
  • A link was clicked.
  • A protected attachment was downloaded.
  • An outbound message was blocked or quarantined.

These notifications depend on your organization’s Trustifi policies.

Note: If you do not receive tracking notifications, it does not necessarily mean the recipient never interacted with the message.

The feature may be disabled, unsupported for that email, or unable to detect the event.

Step 13: Understand Outbound Email Quarantine

TSN Cyber Email Security may block certain outgoing messages based on security policies.

Examples include messages involving:

  • Malicious links.
  • Dangerous attachments.
  • Sensitive information requiring additional protection.
  • Other prohibited content or destinations.

If Your Email Was Blocked

  1. Review any notification.
  2. Confirm the recipient and subject.
  3. Do not repeatedly resend the same message.
  4. Contact True Synergy Networks if the message is legitimate and needed for business.

Important: Do not remove security controls or change the content solely to evade organizational protection rules.

Step 14: Request an Email Delivery Investigation

If the message remains missing, True Synergy Networks can investigate the available delivery records.

Information to Provide

  • Your company name.
  • Your sender email address.
  • The recipient’s email address.
  • The subject line.
  • Approximate sending date and time.
  • Whether the email was encrypted.
  • Whether attachments were included.
  • Any delivery failure notification.
  • Whether the recipient checked Junk or Spam.

Example Support Request

“Hello, I sent an encrypted email to our accountant yesterday around 2:15 PM, but they have not received it. The subject was ‘October Financial Documents.’ I checked Sent Items, and the message is listed there. The recipient has checked their Inbox and Junk folder.”

Important: Do not include confidential attachments, passwords, authentication codes, or other sensitive information in an ordinary support request unless TSN provides an approved secure method.

Understanding Email Trace Retention

Trustifi’s Outbound Email Trace feature retains its delivery trace records for a limited period, documented as 30 days.

Older trace information may no longer be available through that feature.

Your organization may have separate email retention or archiving systems with different retention periods.

Important: Do not assume that email trace logs are a permanent record of all business correspondence.

If you need a formal historical record, contact True Synergy Networks or your organization’s authorized records administrator.

Microsoft Outlook — Check a Missing Sent Message

Step 1: Open Outlook

  1. Open Outlook.
  2. Select your work mailbox.
  3. Open Sent Items.

Step 2: Find the Email

  1. Search by recipient or subject.
  2. Open the message.
  3. Verify the recipient address.
  4. Check the sending time.

Step 3: Review Any Failure Notification

  1. Return to your Inbox.
  2. Search for a delivery failure notice.
  3. Review the error if present.

Step 4: Contact Support

If the message was sent but its delivery cannot be confirmed, contact True Synergy Networks.

Note: Outlook’s Sent Items folder is not a full email-delivery tracking system.

Gmail — Check a Missing Sent Message

Step 1: Open Gmail

  1. Open Gmail.
  2. Sign in to your work account.
  3. Select Sent.

Step 2: Find the Message

  1. Search for the recipient.
  2. Open the email.
  3. Verify the destination address.
  4. Review the date and time.

Step 3: Check for Errors

  1. Review your Inbox.
  2. Search for delivery failure notifications.
  3. Read any returned error.

Step 4: Contact Support

If the email appears to have been sent but the recipient cannot find it, contact True Synergy Networks.

Note: Gmail’s Sent folder does not independently confirm that a recipient opened or read the message.

iPhone or Android — Check Sent Email

Using Outlook

  1. Open the Outlook mobile application.
  2. Select the correct work account.
  3. Open Sent or Sent Items.
  4. Locate the email.
  5. Review the recipient and date.

Using Gmail

  1. Open Gmail.
  2. Select the correct work account.
  3. Open the navigation menu.
  4. Select Sent.
  5. Locate the email.

If more detailed tracking is required, use your approved Trustifi interface when available or contact True Synergy Networks.

Note: Not all Trustifi tracking controls are available directly inside mobile email applications.

Troubleshooting

My Email Is in Sent Items, but the Recipient Never Received It

  1. Verify the recipient address.
  2. Check for a delivery failure notification.
  3. Ask the recipient to check Junk and quarantine.
  4. Confirm whether the email was encrypted.
  5. Contact True Synergy Networks if the message remains missing.

Important: Do not repeatedly resend confidential attachments without investigating the delivery problem.

My Email Says Delivered, but the Recipient Cannot Find It

  1. Confirm which recipient address was used.
  2. Ask the recipient to search their mailbox.
  3. Check Junk or Spam.
  4. Ask whether their organization uses additional email filtering.
  5. Contact True Synergy Networks.

Note: A Delivered event does not guarantee Inbox placement or that the recipient personally read the message.

My Tracking Shows Opened, but the Recipient Says They Did Not Read It

An opening event may be generated by automated email security scanning or privacy-related mail processing.

  1. Do not assume the recipient is mistaken.
  2. Confirm whether automated scanning may have occurred.
  3. Ask the recipient directly if acknowledgment is required.
  4. Contact True Synergy Networks if you need clarification.

Important: Tracking data should not be treated as definitive proof of human readership.

I Cannot See Tracking Information

  1. Confirm that the email was sent through your approved account.
  2. Check whether your organization has enabled tracking.
  3. Verify that you are signed into the correct Trustifi account.
  4. Contact True Synergy Networks.

Note: Some tracking information is only visible to authorized administrators.

My Email Is Stuck in Processing

  1. Confirm the message’s approximate sending time.
  2. Wait briefly for processing.
  3. Check whether a failure notification appears.
  4. Contact True Synergy Networks if processing does not complete.

Important: Do not repeatedly send the message while its status remains uncertain.

My Email Was Quarantined

  1. Review any security notification.
  2. Confirm the subject and recipients.
  3. Contact True Synergy Networks for an authorized review.
  4. Follow the provided instructions.

Important: Do not modify security policies or attempt to bypass outbound filtering.

My Email Failed to Send

  1. Check the recipient address.
  2. Review the returned error message.
  3. Confirm that your internet connection is working.
  4. Check whether the recipient’s address is valid.
  5. Contact True Synergy Networks if the issue persists.

Note: Some delivery failures require investigation of the receiving mail server or sender-side configuration.

I Am Not Receiving Open Notifications

  1. Confirm that message tracking is enabled for your organization.
  2. Check whether notifications are permitted.
  3. Review your Inbox and Junk folder.
  4. Remember that recipient email applications may block tracking.
  5. Contact True Synergy Networks if you require additional information.

Important: The absence of an open notification does not prove that a message was unread.

I Am Not Receiving Attachment Download Notifications

  1. Confirm that the attachment was sent through an approved protected method.
  2. Verify whether download tracking is enabled.
  3. Check for tracking notifications.
  4. Contact True Synergy Networks if necessary.

Note: Tracking availability depends on the message type, security configuration, and recipient behavior.

The Recipient Cannot Open My Encrypted Email

  1. Verify the recipient’s email address.
  2. Confirm that the secure notification was received.
  3. Ask whether authentication was completed.
  4. Check whether the message expired.
  5. Contact True Synergy Networks if the problem continues.

Important: Never ask the recipient to send their verification PIN or account password to you.

My Secure Message Expired

  1. Confirm whether the message is expired.
  2. Verify that the recipient still requires access.
  3. Send a replacement message using approved encryption settings if authorized.

Important: Do not disable required expiration or authentication controls to make the message easier to access.

I Sent an Email to the Wrong Recipient

If sensitive information was sent to an unintended recipient:

  1. Contact True Synergy Networks immediately.
  2. Identify the affected message.
  3. Explain what information was sent.
  4. Follow the approved incident response process.

Important: Do not assume message recall or recipient blocking can remove information already accessed or downloaded.

Trustifi Shows No Record of My Email

  1. Confirm the correct account.
  2. Verify the date and time.
  3. Check whether the message was processed through Trustifi.
  4. Consider whether the event falls outside the available trace retention period.
  5. Contact True Synergy Networks.

Note: Your organization’s mail routing architecture may affect which delivery or tracking events Trustifi records.

Best Practices for Tracking Important Emails

When sending time-sensitive or confidential messages:

  • Verify recipient addresses before sending.
  • Use encryption when required.
  • Enable approved authentication settings.
  • Check Sent Items after sending.
  • Review any delivery failure notifications.
  • Use tracking information as an indicator, not proof of readership.
  • Confirm critical requests directly with the recipient.
  • Use approved electronic signature or acknowledgment systems when formal confirmation is required.
  • Contact True Synergy Networks when delivery cannot be verified.
  • Report accidental disclosures immediately.

Recommendation: For important deadlines, do not rely solely on an Opened or Delivered status. Obtain direct confirmation from the intended recipient.

Additional Information

  • Trustifi supports outbound email activity and delivery tracing.
  • Delivery outcomes may include Delivered, Quarantined, In Process, and Failed.
  • Detailed tracking access depends on user permissions and the organization’s deployment.
  • Supported tracking features can record message openings, link clicks, and protected attachment downloads.
  • Automated security systems may generate opening or link activity events.
  • Delivery does not guarantee Inbox placement or human readership.
  • Trustifi’s Outbound Email Trace feature retains trace logs for 30 days.
  • Secure email access may be affected by expiration, authentication, or recipient access restrictions.
  • Different mail routing configurations provide different levels of delivery status visibility.
  • True Synergy Networks manages email security tracking policies, delivery investigations, and advanced troubleshooting.

Security Reminder: Never assume an email was safely delivered or read simply because a tracking event appeared. Verify important requests through trusted communication channels and avoid repeatedly sending sensitive information when delivery is uncertain. Do not attempt to bypass email security policies, release blocked messages without authorization, or share verification codes. If confidential information was sent to the wrong recipient or you suspect unauthorized access, contact True Synergy Networks immediately.