Outlook not sending out read receipt when i have in enable to be attached to out going emails

Outlook does not provide a log that shows whether a read‑receipt request was attached to each outgoing message. However, several product behaviors from the documentation explain what you are seeing and how to verify configuration:

1. Read‑receipt basics and limitations

• A delivery receipt only confirms delivery to the recipient’s mailbox.
• A read receipt confirms that the message was opened.
• Recipients can decline to send read receipts, and some email programs do not support them.
• There is no way to force a recipient to send a read receipt.

Because of this, even if read‑receipt requests are attached correctly, no receipt may come back, and Outlook will not log a failure.

2. Verify that Outlook is still requesting receipts For Outlook for Windows (classic) on individual messages:
3. Open a new email.
4. On the Options tab, in the Tracking group, select Request a Delivery Receipt and/or Request a Read Receipt.

To ensure this is applied to all messages, follow the guidance under “Be notified when others receive or open an email message” in the article Add and request read receipts and delivery notifications in Outlook.

3. Check recipient‑side behavior Even if Outlook is requesting receipts correctly, receipts may not be returned because:

• The recipient’s Outlook or other client is configured not to send read receipts.
• The recipient is using a client or service that does not support read receipts.
• In some Exchange/OWA scenarios, known issues can prevent read receipts from being sent until specific updates are installed (for example, the Exchange 2010 OWA conversation‑view issue described in the context).

4. Server‑side issues If the environment uses Exchange and receipts show incorrect or unexpected information, transport configuration (for example, DSNConversionMode) can affect how receipts are generated and displayed. In such cases, an Exchange admin can review and adjust transport settings as described in the “Outlook read receipt shows incorrect information” article.
5. Logging options

• Outlook itself does not expose a user‑friendly log specifically for “read‑receipt request attached/not attached.”
• Troubleshooting at the server level (Exchange message tracking logs) is possible only for admins and is outside what Outlook for home users exposes.

In practice, the main checks available are:

• Confirm the Tracking options are enabled on new messages and (if desired) globally.
• Test with a known recipient whose client is configured to “Always send a read receipt” to verify that requests are being honored.
• If using Exchange/OWA, ensure server updates described in the relevant Exchange articles are applied.

References:

• Add and request read receipts and delivery notifications in Outlook
• Add delivery receipt to track an e-mail message
• Outlook read receipt shows incorrect information
• Read receipts are sent from a public folder mailbox instead of from a public folder
• A read receipt is not sent when a receiver does not expand a conversation to preview the message by using OWA in an Exchange Server 2010 environment

Hello

Are you setting up your personal email account, or is it a work/school account?

Are you setting it up for all outbound emails, or it is for individual emails? Best practice recommendation is to request it as needed per email, not for all outbounds. https://support.microsoft.com/en-us/office/add-and-request-read-receipts-and-delivery-notifications-in-outlook-a34bf70a-4c2c-4461-b2a1-12e4a7a92141#picktab=classic_outlook

When you said it didn't work, what's the exact behavior?

As the article above mentioned - "There are other scenarios where read receipts are not sent, such as if the recipient's email program doesn’t support read receipts. There is no way to force a recipient to send a read receipt."