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Funds Held for Clients and Corporate Investments (Narrative) (Details) $ in Millions | 3 Months Ended | 9 Months Ended |
--- | --- | --- | ---
Feb. 28, 2019 USD ($) security | Feb. 28, 2018 USD ($) | Feb. 28, 2019 USD ($) security | Feb. 28, 2018 USD ($) | May 31, 2018 USD ($) security
Schedule of Available-for-sale Securities [Line Items] |  |  |  |  |
Net unrealized losses on available-for-sale securities | $ 9.8 |  | $ 9.8 |  | $ 38.3
Number of available-for-sale securities in an unrealized loss position | security | 667 |  | 667 |  | 970
Gross unrealized losses on available-for-sale securities | $ 17.8 |  | $ 17.8 |  | $ 40.7
Realized gains (losses) on available-for-sale securities | $ 0.4 | $ (0.2) | $ 0.5 | $ (0.6) |
Variable Rate Demand Notes [Member] | Minimum [Member] |  |  |  |  |
Schedule of Available-for-sale Securities [Line Items] |  |  |  |  |
Available-for-sale securities contractual maturities |  |  | 20 years |  |
Variable Rate Demand Notes [Member] | Maximum [Member] |  |  |  |  |
Schedule of Available-for-sale Securities [Line Items] |  |  |  |  |
Available-for-sale securities contractual maturities |  |  | 30 years |  |

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