Hi @Alexkim,
Welcome to Microsoft Q&A, and thank you for reaching out to us.
Please note that as a Microsoft Q&A moderator, I don’t have access to your MacOS configuration, and support for third‑party add-ins such as HubSpot is limited. So I can only provide guidance based on publicly available documentation and resources. That said, I’ll do my best to assist you as much as possible.
From my research, this type of issue is most often caused by third‑party cookies being blocked or cached authentication data becoming corrupted. Based on what you've shared, you’ve already cleared the cache and allowed third‑party cookies without success, so I looked further into similar cases to see if there was anything else that might apply. Unfortunately, I couldn’t find additional information that clearly explains this behavior. We also have limited macOS testing environments, so we’re unable to fully confirm the root cause.
To help narrow things down, if possible, could you confirm whether the same issue appears when using a different browser?
Additionally, does the issue also occur when using the New Outlook desktop app?
In the meantime, I found a related discussion on the HubSpot forums describing a similar issue. I suggest following the steps outlined there to see if it helps resolve the problem.
Note: Microsoft is providing this information as a convenience to you. These sites are not controlled by Microsoft, and Microsoft cannot make any representations regarding the quality, safety, or suitability of any software or information found there. Please ensure that you fully understand the risks before using any suggestions from the above link.
Looking forward to your response.
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