Should have means expectation or failure?

I read the following two lines in a grammar book.

Usage 1. We also use should + have + past participle to talk about an expectation that something happened.

Usage 2. We use should + have + past participle to talk about something that didn't happen in the past and we are sorry that it didn't.

The two sentences sounds ambiguous to me.

Q1. He should have arrived in Jakarta early this morning - Does this mean he arrived according to Usage 1 or he didn't arrive according to Usage 2 or the sentence itself is ambiguous?

Q2. Do we need to add extra context to Q1 like "If the flight was on time, he should have arrived in Jakarta early this morning" to change it to a expectation according to Usage 1?

Regards,

D