This looks like a backend issue that will require more investigation. I would recommend opening a support case for this. https://meraki.cisco.com/meraki-support/overview/
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If you are interested in participating in the EFT for this feature, please take a look at this topic: EFT opportunity: IOS XE upgrades using Cloud Monitoring.
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Windows version. I also opened a support case. The assigned engineer thinks it's likely an SSL inspection issue upstream (i.e on our firewall). Going to check with our security team. Will let you know what I find out.
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We recently created a new demo on Monitoring Catalyst Switches. Check it out. This video is from the Cloud Management & Monitoring for Catalyst course in the Learning Hub.
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