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Hi @cicorias , thanks for reporting this issue. Starting from v2.0.61, Azure CLI restricted the version of applicationinsights to <0.11.8 and caused this issue. We will require same version in next release to resolve this issue.
To avoid this error, you can execute pip install applicationinsights==0.11.7 to install lower version applicationinsights first and then execute pip install iotedgedev to install iotedgedev. In this way pip won't install the latest applicationinsights which breaks the requirement.
Steps to Reproduce:
Output is
Azure cli
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