Consider the following code. It creates an application insight, then it retrieves the instrumentationkey and assigns it to my webapp.
az monitor app-insights component create -g $resourceGroup --app $webapp --application-type web --kind web --tags $defaultTags
$instrumentationKey = az monitor app-insights component show -g $resourceGroup -a $webapp --query 'instrumentationKey' -o tsv
az webapp config appsettings set -g $resourceGroup -n $webapp --settings APPINSIGHTS_INSTRUMENTATIONKEY=$instrumentationKey APPLICATIONINSIGHTS_CONNECTION_STRING=InstrumentationKey=$instrumentationKey
However, this does not turn on application insight for the webapp as shown in this screen capture. I cannot figure out how to turn it on from azure cli.
You need to set a couple more app settings to make it exactly like if you enabled it from the Azure Portal. I believe the second important key after the instrumentation key is ApplicationInsightsAgent_EXTENSION_VERSION
.
Powershell example which you can adapt to AzureCLI:
$app = Get-AzWebApp -ResourceGroupName "AppMonitoredRG" -Name "AppMonitoredSite" -ErrorAction Stop
$newAppSettings = @{} # case-insensitive hash map
$app.SiteConfig.AppSettings | %{$newAppSettings[$_.Name] = $_.Value} # preserve non Application Insights application settings.
$newAppSettings["APPINSIGHTS_INSTRUMENTATIONKEY"] = "012345678-abcd-ef01-2345-6789abcd"; # set the Application Insights instrumentation key
$newAppSettings["APPLICATIONINSIGHTS_CONNECTION_STRING"] = "InstrumentationKey=012345678-abcd-ef01-2345-6789abcd"; # set the Application Insights connection string
$newAppSettings["ApplicationInsightsAgent_EXTENSION_VERSION"] = "~2"; # enable the ApplicationInsightsAgent
$app = Set-AzWebApp -AppSettings $newAppSettings -ResourceGroupName $app.ResourceGroup -Name $app.Name -ErrorAction Stop