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Funds Held for Clients and Corporate Investments (Securities in Unrealized Loss Position) (Details) - USD ($) $ in Millions | Nov. 30, 2018 | May 31, 2018
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Schedule of Available-for-sale Securities [Line Items] |  |
Securities in an unrealized loss position for less than twelve months, Gross unrealized losses | $ (10.2) | $ (27.5)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (36.0) | (13.2)
Total, Gross unrealized losses | (46.2) | (40.7)
Securities in an unrealized loss position for less than twelve months, Fair value | 995.7 | 1,907.0
Securities in an unrealized loss position for more than twelve months, Fair value | 1,253.9 | 331.3
Total, Fair value | 2,249.6 | 2,238.3
Corporate Bonds [Member] |  |
Schedule of Available-for-sale Securities [Line Items] |  |
Securities in an unrealized loss position for less than twelve months, Gross unrealized losses | (4.6) | (6.0)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (6.1) | (1.3)
Total, Gross unrealized losses | (10.7) | (7.3)
Securities in an unrealized loss position for less than twelve months, Fair value | 230.9 | 271.5
Securities in an unrealized loss position for more than twelve months, Fair value | 144.8 | 34.6
Total, Fair value | 375.7 | 306.1
General Obligation Municipal Bonds [Member] |  |
Schedule of Available-for-sale Securities [Line Items] |  |
Securities in an unrealized loss position for less than twelve months, Gross unrealized losses | (2.5) | (8.7)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (9.2) | (2.5)
Total, Gross unrealized losses | (11.7) | (11.2)
Securities in an unrealized loss position for less than twelve months, Fair value | 417.6 | 856.4
Securities in an unrealized loss position for more than twelve months, Fair value | 447.5 | 68.9
Total, Fair value | 865.1 | 925.3
Pre-Refunded Municipal Bonds [Member] |  |
Schedule of Available-for-sale Securities [Line Items] |  |
Securities in an unrealized loss position for less than twelve months, Gross unrealized losses | (0.1) | (0.1)
Total, Gross unrealized losses | (0.1) | (0.1)
Securities in an unrealized loss position for less than twelve months, Fair value | 22.1 | 18.5
Securities in an unrealized loss position for more than twelve months, Fair value | 5.6 | 0.5
Total, Fair value | 27.7 | 19.0
Revenue Municipal Bonds [Member] |  |
Schedule of Available-for-sale Securities [Line Items] |  |
Securities in an unrealized loss position for less than twelve months, Gross unrealized losses | (1.3) | (6.3)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (7.0) | (1.7)
Total, Gross unrealized losses | (8.3) | (8.0)
Securities in an unrealized loss position for less than twelve months, Fair value | 213.9 | 540.9
Securities in an unrealized loss position for more than twelve months, Fair value | 308.1 | 50.9
Total, Fair value | 522.0 | 591.8
U.S. Government Agency Securities [Member] |  |
Schedule of Available-for-sale Securities [Line Items] |  |
Securities in an unrealized loss position for less than twelve months, Gross unrealized losses | (1.7) | (6.4)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (13.7) | (7.7)
Total, Gross unrealized losses | (15.4) | (14.1)
Securities in an unrealized loss position for less than twelve months, Fair value | 111.2 | 219.7
Securities in an unrealized loss position for more than twelve months, Fair value | 347.9 | 176.4
Total, Fair value | $ 459.1 | $ 396.1

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