In San Diego County do Compass cards automatically max out at a day pass rate? Should the total costs of rides eclipse that of a day pass?

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No. According to the MTS page on Compass Cash, the prepaid credit program for Compass Cards:

Each time you tap on Trolley validators, or on the bus fare box for a one-way ticket, the value of that one-way fare will be deducted from your Compass Cash balance. You can deduct multiple one ways during the day or load a Day Pass. [...] Once a Day Pass is loaded, one way fares will no longer be deducted for the remainder of the operational day (for modes that accept the $5.00 day pass).

In other words, there is no automatic fare capping for Day Passes; you must explicitly load a Day Pass when boarding your first bus or at the ticket machine at your first station for rail services to avail the fare cap.

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