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Funds Held for Clients and Corporate Investments (Securities in Unrealized Loss Position) (Details) - USD ($) $ in Millions | Nov. 30, 2017 | May 31, 2017
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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 | $ (12.9) | $ (5.8)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (9.8) |
Total, Gross unrealized losses | (22.7) | (5.8)
Securities in an unrealized loss position for less than twelve months, Fair value | 1,522.5 | 606.4
Securities in an unrealized loss position for more than twelve months, Fair value | 348.3 | 1.0
Total, Fair value | 1,870.8 | 607.4
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 | (1.0) | (0.5)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (0.7) |
Total, Gross unrealized losses | (1.7) | (0.5)
Securities in an unrealized loss position for less than twelve months, Fair value | 117.1 | 43.6
Securities in an unrealized loss position for more than twelve months, Fair value | 35.3 |
Total, Fair value | 152.4 | 43.6
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 | (5.5) | (0.9)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (2.1) |
Total, Gross unrealized losses | (7.6) | (0.9)
Securities in an unrealized loss position for less than twelve months, Fair value | 723.2 | 188.8
Securities in an unrealized loss position for more than twelve months, Fair value | 76.3 |
Total, Fair value | 799.5 | 188.8
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 | 13.4 | 9.2
Securities in an unrealized loss position for more than twelve months, Fair value | 5.8 |
Total, Fair value | 19.2 | 9.2
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 | (4.3) | (0.8)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (1.4) |
Total, Gross unrealized losses | (5.7) | (0.8)
Securities in an unrealized loss position for less than twelve months, Fair value | 478.0 | 154.8
Securities in an unrealized loss position for more than twelve months, Fair value | 52.4 | 1.0
Total, Fair value | 530.4 | 155.8
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 | (2.0) | (3.6)
Securities in an unrealized loss position for more than twelve months, Gross unrealized losses | (5.6) |
Total, Gross unrealized losses | (7.6) | (3.6)
Securities in an unrealized loss position for less than twelve months, Fair value | 190.8 | 210.0
Securities in an unrealized loss position for more than twelve months, Fair value | 178.5 |
Total, Fair value | $ 369.3 | $ 210.0

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- Definition Amount of accumulated unrealized loss on investments in debt and equity securities classified as available-for-sale that have been in a continuous loss position for twelve months or longer. + References Reference 1: http://www.xbrl.org/2003/role/presentationRef -Publisher FASB -Name Accounting Standards Codification -Topic 320 -SubTopic 10 -Section 50 -Paragraph 6 -Subparagraph (a)(2) -URI http://asc.fasb.org/extlink&oid=82897076&loc=d3e27290-111563 Reference 2: http://www.xbrl.org/2003/role/presentationRef -Publisher FASB -Name Accounting Standards Codification -Topic 320 -SubTopic 10 -Section 50 -Paragraph 7 -URI http://asc.fasb.org/extlink&oid=82897076&loc=d3e27337-111563 + Details
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