IoT Edge Deployments should be applied to all devices matching Target Conditions with boolean tags. According to this: "All values in JSON objects can be of the following JSON types: boolean, number, string, object."
Example:
If my edge device twin has the following json tags:
...
"tags": {
"inPortugal": true
}
...
Even though the Portal tells me that the Target Condition will be applied to my device

In the end the Deployment is never applied to the edge device. It works well if I use string:
...
"tags": {
"inPortugal": "yesitis"
}
...

Related issue: https://github.com/MicrosoftDocs/azure-docs/issues/14815
Thanks for the issue report! I followed up with the IoT Hub service team to help investigate this. I'll post again here when I know more.
The IoT Hub service team has confirmed its a bug.
This has been fixed in the IoT Hub service. It is scheduled to be deployed at the beginning of October.
This fix has been deployed to IoT Hub. Closing this issue.