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Desafiador vs. desafiante vs. exigente

While all three words relate to difficulty, their usage depends heavily on regional preference and the specific type of difficulty. Generally, desafiador is preferred in Brazil for stimulating tasks, desafiante is the standard equivalent in Portugal, and exigente is used in both countries to imply strictness or high pressure.

Desafiador

B2
This is the most common adjective in Brazil to describe a situation, task, or object that is difficult but stimulating or inspiring. It implies that the difficulty tests your limits in a way that promotes growth. In Portugal, this word is used less frequently, as locals prefer desafiante.
O novo projeto é complexo e muito desafiador.
(The new project is complex and very challenging.)
Mudar de carreira aos quarenta anos pode ser desafiador.
(Changing careers at forty can be challenging.)
Enfrentamos um cenário econômico desafiador este ano.
(We are facing a challenging economic scenario this year.)
Este jogo tem um nível muito desafiador para iniciantes.
(This game has a very challenging level for beginners.)

Desafiante

B2
In Portugal, this is the standard word for challenging regarding tasks or situations (synonymous with the Brazilian usage of desafiador). However, in Brazil, desafiante is more commonly used as a noun to describe a challenger or opponent in a competition, rather than an adjective for a situation.
Foi uma experiência extremamente desafiante para a equipe.
(It was an extremely challenging experience for the team.)
Os trilhos daquela montanha são bonitos mas desafiantes.
(That mountain's trails are beautiful but challenging.)
O atual campeão derrotou o desafiante no primeiro round.
(The current champion defeated the challenger in the first round.)
Este puzzle é bastante desafiante e requer paciência.
(This puzzle is quite challenging and requires patience.)

Exigente

B1
Used in both Brazil and Portugal, this word translates to demanding or strict. Unlike the previous words, which focus on the hurdle or the adventure, exigente focuses on the high standards, pressure, or perfectionism required. It applies to both tasks (requiring effort) and people (requiring high standards from others).
O curso de medicina é muito exigente e longo.
(Medical school is very demanding and long.)
O meu chefe é muito exigente com os prazos de entrega.
(My boss is very demanding regarding delivery deadlines.)
A agenda do presidente é extremamente exigente.
(The president's schedule is extremely demanding.)
Ela é uma cliente exigente que aceita a melhor qualidade.
(She is a demanding client who only accepts the best quality.)

Summary

To sound natural: use desafiador in Brazil and desafiante in Portugal when describing a difficult but stimulating task. Use exigente in both countries when describing something or someone that demands high standards, strictness, or intense effort.