überhaupt
at all
Used in negative sentences and questions to generalize or intensify a statement; often in the sense of 'gar' (not at all) or 'at all'.
Ich habe heute überhaupt keine Zeit für ein Treffen.
I have no time at all for a meeting today.

at all / generally
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at all
Used in negative sentences and questions to generalize or intensify a statement; often in the sense of 'gar' (not at all) or 'at all'.
Ich habe heute überhaupt keine Zeit für ein Treffen.
I have no time at all for a meeting today.

'Überhaupt' is made up of 'über' (over) and 'Haupt' (head). The literal idea is 'looked over the head', which makes the meaning 'by and large' or 'generally' understandable.
Wir müssen überhaupt erst einmal klären, was das Ziel ist.
First of all, we need to clarify what the goal is.
In negative sentences, 'überhaupt' intensifies the negation. It often comes directly before the negated part, in the combinations 'überhaupt nicht' (not at all) or 'überhaupt kein/e' (no ... at all).
Ich kann mich überhaupt nicht an seinen Namen erinnern.
I can't remember his name at all.
In a question, 'überhaupt' often expresses doubt, surprise, or impatience. It calls the basis of the question or a prerequisite into question.
Weißt du überhaupt, wie spät es ist?
Do you even know what time it is?
'Überhaupt' can introduce a general or fundamental statement. It then means something like 'in general' or 'in principle'.
Die Lage auf dem Wohnungsmarkt ist überhaupt sehr angespannt.
The situation on the housing market is generally very tense.
The expression 'wenn überhaupt' (if at all) strongly limits a statement and expresses that something is very rare or unlikely. It means 'if it happens at all'.
Er meldet sich nur selten, und wenn überhaupt, dann nur per SMS.
He only rarely gets in touch, and if at all, then only by text message.
because
'denn' and 'überhaupt' can both appear in questions and show an attitude. 'denn' often makes the question sound friendlier, more interested, or more personal. 'überhaupt' intensifies the question more strongly and often shows doubt, surprise, or impatience. In 'Was meinst du denn?' (What do you mean, then?), the question sounds more open. In 'Was meinst du überhaupt?' (What do you even mean?), it often sounds more critical or impatient. Learners may confuse the words because both are small words used in questions. As a guide: 'denn' makes the question softer, while 'überhaupt' makes it stronger.

Warum rufst du mich überhaupt so spät an?
Why are you even calling me this late?
Wo hast du denn dein Fahrrad abgestellt?
Where did you park your bike, then?