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Sharing Alexander's upbringing, Hephaestion would have learned to fight and to ride well from an early age. His first taste of military action was probably the campaign against the Thracians while Alexander was regent, followed by Philip II's Danube campaign, and the battle of Chaeronea (338 BC) while he was still in his teens. His name is not mentioned in lists of high-ranking officers during the early battles of Alexander's Danube campaign, or the invasion of Persia, and nor are the names of Alexander's other close friends and contemporaries, suggesting that their promotions, when they achieved them, were earned by merit.

Hephaestion's career was never solely a military one. Right from the start, he was also engaged in special missions, sometimes diplomatic, sometimes technical. The first mention of his career in the sources is a diplomatic mission of some importance. After the battle of Issus (333 BC), when Alexander was proceeding south down the Phoenician coast and had received the capitulation of Sidon, Hephaestion was "... authorised to appoint to the throne the Sidonian he considered most deserving of that high office." Hephaestion took local advice, and chose a man distantly related to the royal family, but whose honesty had reduced him to working as a gardener. The man, Abdalonymus, had a successful royal career, fully justifying Hephaestion's choice.

After the siege of Tyre (332 BC), Alexander entrusted his fleet to Hephaestion, who had orders to skirt the coast and head for Gaza, their next objective, while Alexander himself led the army overland. Hephaestion's task was not an easy one, for this was not the Athenian fleet with which Alexander had started, and had earlier disbanded, but a motley collection of semi-reluctant allies of many nationalities, who would need holding together with patience and strength. Furthermore, on arrival at Gaza, the cargo of siege engines had to be unloaded, transported across difficult terrain, and reassembled.

Plutarch, while writing about Alexander's correspondence, reveals an occasion when Hephaestion was away on business, and Alexander wrote to him. The subject matter suggests that this took place while they were in Egypt. What business Hephaestion was attending to we do not know, but Andrew Chugg has suggested that it was concerned either with his command of the fleet or Athenian diplomacy. He quotes sources, which suggest that Hephaestion had been approached by Aristion of Athens to effect a reconciliation between Alexander and Demosthenes, and certainly, Athens' inaction during the Spartan revolt would seem to support the idea. As Chugg says, "If he did persuade Alexander to reach an accommodation with Demosthenes at this critical juncture, as would seem likely from the circumstances, then he was significantly responsible for saving the situation for Macedon in Greece by preventing the revolt of Agis spreading to Athens and her allies."

It is likely, though not certain, that it was Hephaestion who led the advance army from Egypt to bridge the Euphrates river. Darius of Persia sent Mazaeus to hold the opposite bank while the bridging work was in progress. This Mazaeus was the commander who threw away what looked like certain victory on the Persian right at the battle of Gaugamela (331 BC), and later became Alexander's governor of Babylon. Robin Lane Fox has an interesting suggestion that conversation with Hephaestion may have won Mazaeus over: "It is conceivable that the battle of Gaugamela was partly won on the banks of the Euphrates and that Mazaeus' reinstatement was less a sign of magnanimity than of a prearranged reward."

It is at Gaugamela that mention is first made of Hephaestion's rank. He is called the "&hellip; commander of the bodyguards (somatophylakes)." This is not the Royal Squadron, whose duties also included guarding the king in battle, and which was at that time commanded by Cleitus&mdash;a man of the older generation&mdash;but a small group of close companions specifically designated to fight alongside the king. Hephaestion was certainly in the thick of things with Alexander, for Arrian tells us he was wounded, and Curtius specifically mentions that it was a spear wound in the arm.

After Gaugamela, there is the first indication that Alexander intended reconciliation with the Persians, and that Hephaestion supported him in this unpopular policy. One evening in Babylon, Alexander noticed a high-born woman obliged to dance as part of the entertainment. Curtius explains: "The following day, he (Alexander) instructed Hephaestion to have all the prisoners brought to the royal quarters and there he verified the lineage of each of them." Alexander had realised that people from noble families were being treated with little dignity, and wanted to do something about it. That he chose Hephaestion to help him shows that he could rely on Hephaestion's tact and sympathy. Yet Alexander could also rely on Hephaestion for firmness and resolve. When his policies had led to a plot against his life, the possible involvement of a senior officer, Philotas, caused much concern. It was Hephaestion, along with Craterus and Coenus, who insisted on, and actually carried out, the customary torture.

After the execution of Philotas (330 BC), Hephaestion was appointed joint commander&mdash;with Cleitus&mdash;of the Companion cavalry, Philotas' former position. This dual appointment was a way of satisfying two divergent shades of opinion now hardening throughout the army, one, like Hephaestion, broadly supportive of Alexander's policy of integration, and the other, that of Philip's older veterans in particular, whose implacable resentment of Persian ways was well-represented by Cleitus. The cavalry prospered under this command, showing itself equal to learning new tactics, necessary against Scythian nomads, and to counter-insurgency measures such as those deployed in the spring of 328 BC. The army set out from Balkh in five columns, to spread through the valleys between the Oxus and Tanais rivers, to pacify Sogdiana. Hephaestion commanded one of the columns, and after arriving at Marakanda, he set out again to establish settlements in the region.

In spring 327 BC, the army headed into India, and Alexander divided his forces. He led his section north into the Swat valley, while Hephaestion and Perdiccas took a sizeable contingent through the Khyber Pass. Hephaestion's orders were to "&hellip; take over either by force or agreement all places on their march, and on reaching the Indus to make suitable preparations for crossing." They were in unknown territory, whose political and geographical landscapes were unfamiliar, and Hephaestion would have had to make decisions on the spot, and act accordingly. He reached the Indus with the land behind him conquered, including the successful siege of Peuceolatis, which took thirty days, and proceeded to organise the construction of boats for the crossing.

Alexander often had to divide his forces, and command was given to a variety of senior officers on different occasions. For example, a few weeks before this mission of Hephaestion's, Craterus had been sent with a large force to subdue the last two remaining Bactrian rebels. It seems that Hephaestion was chosen when the objectives were far from clear-cut, and Alexander needed a commander on whom he could rely to do what he would have done himself, without needing instructions.

Hephaestion took part in a notable cavalry charge at the battle of the Hydaspes (326 BC) and then, when the army began its homeward journey, was again entrusted with half the army, including the elite troops and two hundred elephants, as they travelled south-west along the banks of the Hydaspes. Some of the army, including Alexander himself, travelled in boats, which had been provided by the sponsorship of leading courtiers. Arrian lists Hephaestion first among these "honorary trierarchs", indicating his leading position at this time. On entering hostile territory, Alexander split his forces into three. Hephaestion's section marched "&hellip; five days in advance, with the object of intercepting and capturing any native troops which &hellip; might be rapidly moving forward". Again, Hephaestion was called upon when initiative was required. After Alexander had taken a detour to subdue a hostile tribe, in which he was seriously injured, Hephaestion took command of the greater part of the army as they travelled down the Indus to the sea. At the coast, he organised the construction of a fortress, and a harbour for the fleet at Pattala.

Hephaestion was in command at Pattala, while Alexander advanced. When he rejoined Alexander at Rhambacia, he established a city there also. Hephaestion crossed the Gedrosian desert with Alexander, sharing the torments of that journey, and when the army was safely back in Susa, he was decorated for bravery. He was to take part in no further fighting; he had only months to live. But, having ended his military career as Alexander's de facto second-in-command, he was also his second in the political sphere. Alexander had made that official by naming him chiliarch. Photius' Epitome of Arrian's Events after Alexander mentions Perdiccas being appointed "&hellip; to command the chiliarchy which Hephaestion had originally held."