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For 67 years, from 197 BC to 133 BC, the most difficult provinces to control were Hispania Citerior and Hispania Ulterior in Hispania (Spain and Portugal). There were numerous rebellions by the local tribes and the Romans constantly had to fight to suppressed them. The situation got so bad that at one point many Romans found excuses to avoid the draft because Hispania had become like a graveyard for Romans. The locals used guerrilla tactics. Victories in 139 BC and 133 BC led to the pacification of eastern southern and central Spain. The Romans faced another major rebellion in the north which lasted ten years (The Cantabrian War, 29-19 BC). After its suppression the whole of Hispania was pacified.

From 14 BC to 9 AD the most difficult province to control was Illyricum, where they faced two major rebellions: the Pannonian War (14-10 BC) and the Batonian War (6-9 AD). The latter was one of the biggest rebellions the Roman faced in the whole of their history and was described as the most serious war since the Second Punic War (218-201 BC). It even caused fears about the security of nearby Italy.

After that the most difficult provinces to control were Judea, Syria, Osroene and Mesopotamia. In Judea the Romans faced a number of major rebellions by the Jews: the Great Revolt of 63-73, the Bar Kokhba revolt of 132-136, and the Kitos War 115-117. After the pacification of provinces in the west and of Illyricum, Judea was the only province where there were major rebellions. The other provinces became well integrated with the Roman Empire partly because the Romans respected local religions, laws and customs and allowed the local elites to run affairs at the local level according to their traditions and laws and partly because many provinces benefitted from the thriving trade which developed in the empire and beyond. The problem in Syria, Osroene and Mesopotamia was one of internal rebellion. It was their being on the border with the Persian Empire. There were many wars between the Romans and the Persians and the latter often overrun these provinces.

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The border provinces along the Rhine and Danube Rivers, the Levant and Africa.

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Q: Which Roman provinces might be the most difficult for the Roman Empire to keep cotrol over Why?
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Which Roman provinces were the most difficult for the Roman empire to keep control over?

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