I am unable to click on a link in my Outlook messages despite allowing popups in my settings.

Question

I am unable to click on a link in my Outlook messages despite allowing popups in my settings.

Bill Stahl 25

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Answer accepted by question author

Anonymous

Hi, I understand how inconvenient it is when links won’t open in Outlook even after allowing pop-ups. This usually happens because Outlook is displaying emails in plain text or security features like Safe Links are rewriting URLs and blocking them. First, check if Outlook is set to read messages in plain text by going to File > Options > Trust Center > Trust Center Settings > Email Security and make sure that option is turned off. Next, try opening the same email in Outlook Web, if links work there, the issue is with the desktop client. Also, do you notice the links starting with https://safelinks.protection.outlook.com/ when you hover over them? That would confirm Safe Links is active. Are you using any antivirus or add-ins that might block links? Let me know what you find so we can narrow this down.Regards,
Aron

Bill Stahl 25 Reputation points

2025-12-15T14:42:39.8866667+00:00

Aron, I appreciate your response. However, I don't see File > Options > Trust Center > Trust Center Settings > Email Security available to me. Where would I find this screen? (See attached screenshot). Thanks!
Anonymous

2025-12-15T14:45:50.6133333+00:00

Thanks for clarifying! The menu I mentioned only appears in the Windows desktop version of Outlook, so if you’re on Mac or using Outlook Web, those options won’t be there because link behavior is managed differently.

On Mac, you can check under Preferences > Reading to make sure emails aren’t set to display in plain text, as that disables clickable links.

If you’re on Outlook Web, the issue is usually caused by Microsoft 365 Safe Links policies, which rewrite URLs for security, hover over a link and see if it starts with https://safelinks.protection.outlook.com.

If it does, it’s a policy setting rather than something you can change locally.

Could you confirm which version you’re using so I can give you the exact steps to fix this?
Bill Stahl 25 Reputation points

2025-12-15T14:53:25.85+00:00

Thanks, Aron. I'm using Safari version 26.1
Anonymous

2025-12-15T14:55:53.6266667+00:00

Thanks for sharing that detail!

Since you’re using Safari, it means you’re likely accessing Outlook on the web, and that explains why you don’t see the Trust Center options, they’re only available in the Windows desktop app.

In Outlook Web, link behavior is controlled by Microsoft 365 security policies like Safe Links, which rewrite URLs for protection.

To confirm, hover over a link and check if it starts with https://safelinks.protection.outlook.com; if it does, the policy is active, and links should still open unless your organization has restricted them.

If links don’t respond at all, try clearing Safari’s cache and cookies, disabling any browser extensions that might block scripts, and testing in a private window.

Can you check if the links show the Safe Links format and let me know if you’re using a personal account or a work/school account?

That will help me guide you to the right fix.

Regards,
Aron
Bill Stahl 25 Reputation points

2025-12-15T15:03:14.1966667+00:00

This is a personal account. I have attached a screenshot of what appears when I hover over a link. Thanks!
Anonymous

2025-12-15T15:07:08.8+00:00

Thanks for confirming and sharing the screenshot!

Since you’re using a personal account in Outlook Web via Safari, the Trust Center settings aren’t available because link handling is managed by Microsoft’s security features, not local settings.

From what you described, if the link preview shows a normal URL and not one starting with https://safelinks.protection.outlook.com/, then Safe Links isn’t involved, and the issue is likely browser related.

Try clearing Safari’s cache and cookies, disabling any extensions that might block scripts, and testing in a private window to rule out interference.

If links still don’t open, can you check if the same email works in another browser like Chrome or Edge?

That will help confirm if this is a Safari-specific issue or something else.

Regards,
Aron
Bill Stahl 25 Reputation points

2025-12-15T15:32:59.27+00:00

The screenshot I sent seems to indicate that safelinks is involved, doesn't it?
Anonymous

2025-12-15T15:36:25.24+00:00

If links in your Outlook Web emails won’t open in Safari, it’s usually due to browser settings or security features rather than Outlook itself. Start by allowing pop-ups for Outlook in Safari under Settings > Websites > Pop-up Windows, then clear Safari’s cache and cookies to remove any corrupted data. Disable any browser extensions like ad blockers or privacy tools that might block scripts, and if you use iCloud Private Relay, turn it off temporarily as it can interfere with link behavior. Test Outlook in a private window or another browser like Chrome or Edge to see if the issue is Safari-specific, and if links work there, you’ll know it’s a browser setting. As a fallback, using the Outlook desktop or mobile app avoids these restrictions entirely. Can you check if the links show the correct URL when you hover over them and confirm if any extensions are active? That will help narrow down the cause.
Bill Stahl 25 Reputation points

2025-12-15T15:52:26.19+00:00

I cleared my Safari cache and cookies, and I now do seem to be able to successfully click on the links in emails. Hopefully that will stay. Thanks very much for your help!
Anonymous

2025-12-15T16:26:43.2533333+00:00

I hope this information is helpful. If you have any further questions or need additional assistance, please reach back out and I will be more than happy to assist you.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

Regards,

Aron
Bill Stahl 25 Reputation points

2025-12-22T18:17:27.21+00:00

I'm still having issues. Every couple of days or whenever I reboot my computer, I again get the pop-up blocked message in my messages. I clear out my cookies, which creates more issues. But eventually I again get the pop-up blocked messages again. Any other ideas?

1 additional answer

Your answer

Bill Stahl 25 Reputation points

2025-12-15T14:42:39.8866667+00:00

Aron, I appreciate your response. However, I don't see File > Options > Trust Center > Trust Center Settings > Email Security available to me. Where would I find this screen? (See attached screenshot). Thanks!
Anonymous

2025-12-15T14:45:50.6133333+00:00

Thanks for clarifying! The menu I mentioned only appears in the Windows desktop version of Outlook, so if you’re on Mac or using Outlook Web, those options won’t be there because link behavior is managed differently.

On Mac, you can check under Preferences > Reading to make sure emails aren’t set to display in plain text, as that disables clickable links.

If you’re on Outlook Web, the issue is usually caused by Microsoft 365 Safe Links policies, which rewrite URLs for security, hover over a link and see if it starts with https://safelinks.protection.outlook.com.

If it does, it’s a policy setting rather than something you can change locally.

Could you confirm which version you’re using so I can give you the exact steps to fix this?
Bill Stahl 25 Reputation points

2025-12-15T14:53:25.85+00:00

Thanks, Aron. I'm using Safari version 26.1
Anonymous

2025-12-15T14:55:53.6266667+00:00

Thanks for sharing that detail!

Since you’re using Safari, it means you’re likely accessing Outlook on the web, and that explains why you don’t see the Trust Center options, they’re only available in the Windows desktop app.

In Outlook Web, link behavior is controlled by Microsoft 365 security policies like Safe Links, which rewrite URLs for protection.

To confirm, hover over a link and check if it starts with https://safelinks.protection.outlook.com; if it does, the policy is active, and links should still open unless your organization has restricted them.

If links don’t respond at all, try clearing Safari’s cache and cookies, disabling any browser extensions that might block scripts, and testing in a private window.

Can you check if the links show the Safe Links format and let me know if you’re using a personal account or a work/school account?

That will help me guide you to the right fix.

Regards,
Aron
Bill Stahl 25 Reputation points

2025-12-15T15:03:14.1966667+00:00

This is a personal account. I have attached a screenshot of what appears when I hover over a link. Thanks!
Anonymous

2025-12-15T15:07:08.8+00:00

Thanks for confirming and sharing the screenshot!

Since you’re using a personal account in Outlook Web via Safari, the Trust Center settings aren’t available because link handling is managed by Microsoft’s security features, not local settings.

From what you described, if the link preview shows a normal URL and not one starting with https://safelinks.protection.outlook.com/, then Safe Links isn’t involved, and the issue is likely browser related.

Try clearing Safari’s cache and cookies, disabling any extensions that might block scripts, and testing in a private window to rule out interference.

If links still don’t open, can you check if the same email works in another browser like Chrome or Edge?

That will help confirm if this is a Safari-specific issue or something else.

Regards,
Aron
Bill Stahl 25 Reputation points

2025-12-15T15:32:59.27+00:00

The screenshot I sent seems to indicate that safelinks is involved, doesn't it?
Anonymous

2025-12-15T15:36:25.24+00:00

If links in your Outlook Web emails won’t open in Safari, it’s usually due to browser settings or security features rather than Outlook itself. Start by allowing pop-ups for Outlook in Safari under Settings > Websites > Pop-up Windows, then clear Safari’s cache and cookies to remove any corrupted data. Disable any browser extensions like ad blockers or privacy tools that might block scripts, and if you use iCloud Private Relay, turn it off temporarily as it can interfere with link behavior. Test Outlook in a private window or another browser like Chrome or Edge to see if the issue is Safari-specific, and if links work there, you’ll know it’s a browser setting. As a fallback, using the Outlook desktop or mobile app avoids these restrictions entirely. Can you check if the links show the correct URL when you hover over them and confirm if any extensions are active? That will help narrow down the cause.
Bill Stahl 25 Reputation points

2025-12-15T15:52:26.19+00:00

I cleared my Safari cache and cookies, and I now do seem to be able to successfully click on the links in emails. Hopefully that will stay. Thanks very much for your help!
Anonymous

2025-12-15T16:26:43.2533333+00:00

I hope this information is helpful. If you have any further questions or need additional assistance, please reach back out and I will be more than happy to assist you.

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

Regards,

Aron
Bill Stahl 25 Reputation points

2025-12-22T18:17:27.21+00:00

I'm still having issues. Every couple of days or whenever I reboot my computer, I again get the pop-up blocked message in my messages. I clear out my cookies, which creates more issues. But eventually I again get the pop-up blocked messages again. Any other ideas?

Answer 1

If you are unable to click on links in your Outlook messages, it may be related to security settings or restrictions in your system. After installing the July 11th security updates for Outlook, users may encounter issues when trying to open hyperlinks that point to Fully Qualified Domain Names (FQDN) or IP addresses, receiving error messages such as "Something unexpected went wrong with this URL." Additionally, if Internet Explorer is set as your default browser, you might see messages indicating that your organization's policies are preventing the action.

To troubleshoot this issue, you can try resetting your Internet Explorer settings, as this can sometimes resolve hyperlink issues in Outlook. Here are the steps you can follow:

Open Internet Explorer and go to Tools > Internet Options.
Navigate to the Advanced tab and select Reset.
In the Reset Internet Explorer Settings window, check Delete personal settings and then click Reset.
After the reset is complete, restart Internet Explorer and check if the issue persists.

If the problem continues, you may need to check your organization's policies or contact your IT support for further assistance.

References: