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I've been asking this question many German natives but I received very contradicting feedback. Maybe I am asking in a bad way.

In English when you say

"He should have done this"

it can mean one of 2 things:

  1. He didn't do, it was important though, he should have done it.

  2. He intended to do it, he said he was going to do it, he should have done it by now. I am not sure though whether he have done it or not.

So how do these relate to the German sentences:

Er sollte das machen

Er hätte das machen sollen

Er hätte das machen müssen

Er soll das gemacht haben

Er muss das gemacht haben

Also, I want to know the passive form of these meanings. So what is the German alternative for:

  1. This should have been done (It wasn't done, and I am pissed)

  2. This should have been done (Someone said he was going to do it, not sure though)

2

The first meaning (not time related) could be translated as

Er hätte es/das machen sollen/müssen.

Er hätte es/das gemacht haben müssen.

However, the second one is a very complicated construct which is not used very often.

Also the following fits:

Er hätte es/das besser gemacht.

Besser wäre es gewesen, hätte er es/das gemacht.

Although this has a very similar meaning, technically it is a different sentence (in English: It would have been better to do it).

The second meaning (time related) could be related to:

Er sollte es/das gemacht haben [bis jetzt/heute].

In German, usually additional phrases like bis jetzt (by now) are used to express the meaning more clearly.

The other sentences you provided do not fit, since they have a different meaning:

Er sollte es/das machen.

He was supposed to do it/this.

Er muss es/das gemacht haben.

He must have done it/this.

Both passive forms can be expressed as

Es/Das hätte gemacht werden sollen.

However, to express the I am pissed meaning you can use müssen instead of sollen and to express the time related meaning again you can use an additional phrase like bis jetzt:

Es/Das hätte bis jetzt/heute gemacht werden sollen.

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