Isaac ibn Khalfun (b. ca. 990) was one of the earliest of the “Golden Age” Hebrew poets in al-Andalus, and the only professional Hebrew poet known to us from this period. Though today he is perhaps best-known for the poems which he exchanged with Samuel ha-Nagid of Granada, he was also a wandering poet who travelled through North Africa and the eastern Mediterranean in search of rich patrons. His travels brought him into contact with some of the most illustrious Jews of the age, such as Manasseh ibn al-Kazaz of Damascus, and Abraham ben Nathan and Rabbi Nissim ben Jacob of Kairouan. Though highly regarded in medieval times, Ibn Khalfun's poetry eventually fell into oblivion and was only rediscovered in the twentieth century thanks to the discoveries of the Cairo Geniza. This study analyzes Ibn Khalfun's poems from a literary, social and cultural standpoint. Though he practiced many of the same genres penned by other, non-professional poets in al-Andalus (such as the panegyric), his professional status finds striking expression in almost two dozen “payment poems;” a genre which is almost unique to Ibn Khalfun in Hebrew letters, but common among the professional Arabic poets of his own day and age. This study also examines such issues as literary patronage in Jewish society, the role of the poet in the courtly milieu, and the poet's perception of his art. From all the available data, it appears that the poems found in the Cairo Geniza represent Ibn Khalfun's wandering years outside of al-Andalus rather than a portion of the poet's official dīwān, as is generally assumed in the research. This suggests that the production of secular Hebrew poetry was not limited to the Iberian peninsula even at this early date, as is commonly believed, and that apart from the poems to Samuel ha-Nagid, the main body of Ibn Khalfun's works—the poems composed in al-Andalus remain lost to us.