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I have created the following subscription. If I make an update via WebAPI to an Opportunity with an Objective of "Reach Lead" I receive a webhook.

If however I make the same change to the same Opportunity via the web front-end I receive no webhook.

If I have no filter set I receive webhook events in both cases.

{
"Data": {
"Item": {
"SubscriptionId": "edbbe827-19ff-4bbb-85a5-11aa717a9966",
"Entity": "Opportunity",
"Op": "Update",
"TargetId": "d6936eec-0d35-4e64-82d0-2fbd1052ed84",
"Recipients": [],
"Filter": [
{
"Objective": {
"$EQ": "Reach Lead"
}
}
]
}
}
}