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Many customer have question regarding this issue, where they use notify member option before, never had problem, but now they have. The answer is related to ConnectWise's API design.
ConnectWise had 3 API. (v1.5, v2.0 and v3.0).
v1.5 SOAP API, payload is XML SOAP envelop.
v2.0 SOAP API, payload is XML SOAP envelop.
v3.0 RESTful API, payload is JSON.
v1.5 and v2.0 are pretty much similar. But v3.0 is completely different beast. The fundamental difference is not only from its payload but also from its perspective.
v1.5 and v2.0 They focus on general purpose API. That means the perspective or personality of the API is stand at neutral point of view. Where itself is not act on behalf of any user. In that way, you can use API to create ticket on behalf of any user, include contact, or member.
v3.0 The root of this API is from member point of view. Even the authorization is from API member. That means any API been used is act on behalf of API member. It is not stand as neutral.
When creating ticket or ticket note through API v3.0, from ConnectWise system point of view, it is always created by a member. Even though it is API member. This cause huge problem from the end result. It causes following problems.
Notify member not been triggered. Because note is added by API member as member, not as contact.
Initial description of ticket is logged by API member, not contact. It's just because it is API member who created ticket. API member is a human.
Ticket received email, Note added email all display they are logged by API member. Author is also API member. Because API member is human.
Until ConnectWise introduce additional API to resolve those perspective issue, it will be something that is hard to resolve.
Here is more technical point of view. For API design, ConnectWise's RESTful API design have problem start at routing.
Tickets routing is under: /service/tickets. For such routing, it can only act on behalf of itself (API member) or on behalf of nothing.
Other kind of design could be following.
/contacts/{contactId}/service/tickets. This means we want to get tickets by that contact, or create ticket by that contact.
/members/{memberId}/service/tickets. Similar as contact, this is on behalf of member.
/service/tickets. This is for general purpose, serve as admin that can access to all tickets. Or create ticket by system.
This issue is related to ConnectWise APIv3, where the new API does not respect Service Board's notify member setting.
The work around is to use Automatic Email options in following setting
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