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Funds Held for Clients and Corporate Investments (Securities in Unrealized Loss Position) (Details) - USD ($) $ in Millions | Feb. 28, 2019 | 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 | $ (0.6) | $ (27.5)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (17.2) | (13.2)
Total, Gross unrealized losses | (17.8) | (40.7)
Securities in an unrealized loss position for less than twelve months, Fair value | 134.0 | 1,907.0
Securities in an unrealized loss position for more than twelve months, Fair value | 1,319.6 | 331.3
Total, Fair value | 1,453.6 | 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 | (0.1) | (6.0)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (4.2) | (1.3)
Total, Gross unrealized losses | (4.3) | (7.3)
Securities in an unrealized loss position for less than twelve months, Fair value | 23.0 | 271.5
Securities in an unrealized loss position for more than twelve months, Fair value | 262.4 | 34.6
Total, Fair value | 285.4 | 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 | (0.1) | (8.7)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (2.5) | (2.5)
Total, Gross unrealized losses | (2.6) | (11.2)
Securities in an unrealized loss position for less than twelve months, Fair value | 56.2 | 856.4
Securities in an unrealized loss position for more than twelve months, Fair value | 397.8 | 68.9
Total, Fair value | 454.0 | 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)
Total, Gross unrealized losses |  | (0.1)
Securities in an unrealized loss position for less than twelve months, Fair value | 0.1 | 18.5
Securities in an unrealized loss position for more than twelve months, Fair value | 5.5 | 0.5
Total, Fair value | 5.6 | 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 |  | (6.3)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (1.9) | (1.7)
Total, Gross unrealized losses | (1.9) | (8.0)
Securities in an unrealized loss position for less than twelve months, Fair value | 13.2 | 540.9
Securities in an unrealized loss position for more than twelve months, Fair value | 273.5 | 50.9
Total, Fair value | 286.7 | 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 | (0.4) | (6.4)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (8.6) | (7.7)
Total, Gross unrealized losses | (9.0) | (14.1)
Securities in an unrealized loss position for less than twelve months, Fair value | 41.5 | 219.7
Securities in an unrealized loss position for more than twelve months, Fair value | 380.4 | 176.4
Total, Fair value | $ 421.9 | $ 396.1

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