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The Bouncy Castle Java APIs for TLS and DTLS, including a provider for the JSSE.
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package org.bouncycastle.tls;

class Timeout
{
    private long durationMillis;
    private long startMillis;

    Timeout(long durationMillis)
    {
        this(durationMillis, System.currentTimeMillis());
    }

    Timeout(long durationMillis, long currentTimeMillis)
    {
        this.durationMillis = Math.max(0, durationMillis);
        this.startMillis = Math.max(0, currentTimeMillis);
    }

//    long remainingMillis()
//    {
//        return remainingMillis(System.currentTimeMillis());
//    }

    synchronized long remainingMillis(long currentTimeMillis)
    {
        // If clock jumped backwards, reset start time 
        if (startMillis > currentTimeMillis)
        {
            startMillis = currentTimeMillis;
            return durationMillis;
        }

        long elapsed = currentTimeMillis - startMillis;
        long remaining = durationMillis - elapsed;

        // Once timeout reached, lock it in
        if (remaining <= 0)
        {
            return durationMillis = 0L;
        }

        return remaining;
    }

//    static int constrainWaitMillis(int waitMillis, Timeout timeout)
//    {
//        return constrainWaitMillis(waitMillis, timeout, System.currentTimeMillis());
//    }

    static int constrainWaitMillis(int waitMillis, Timeout timeout, long currentTimeMillis)
    {
        if (waitMillis < 0)
        {
            return -1;
        }

        int timeoutMillis = getWaitMillis(timeout, currentTimeMillis);
        if (timeoutMillis < 0)
        {
            return -1;
        }

        if (waitMillis == 0)
        {
            return timeoutMillis;
        }
        if (timeoutMillis == 0)
        {
            return waitMillis;
        }

        return Math.min(waitMillis, timeoutMillis);
    }

    static Timeout forWaitMillis(int waitMillis)
    {
        return forWaitMillis(waitMillis, System.currentTimeMillis());
    }

    static Timeout forWaitMillis(int waitMillis, long currentTimeMillis)
    {
        if (waitMillis < 0)
        {
            throw new IllegalArgumentException("'waitMillis' cannot be negative");
        }
        if (waitMillis > 0)
        {
            return new Timeout(waitMillis, currentTimeMillis);
        }
        return null;
    }

//    static int getWaitMillis(Timeout timeout)
//    {
//        return getWaitMillis(timeout, System.currentTimeMillis());
//    }

    static int getWaitMillis(Timeout timeout, long currentTimeMillis)
    {
        if (null == timeout)
        {
            return 0;
        }
        long remainingMillis = timeout.remainingMillis(currentTimeMillis);
        if (remainingMillis < 1L)
        {
            return -1;
        }
        if (remainingMillis > Integer.MAX_VALUE)
        {
            return Integer.MAX_VALUE;
        }
        return (int)remainingMillis;
    }

//    static boolean hasExpired(Timeout timeout)
//    {
//        return hasExpired(timeout, System.currentTimeMillis());
//    }

    static boolean hasExpired(Timeout timeout, long currentTimeMillis)
    {
        return null != timeout && timeout.remainingMillis(currentTimeMillis) < 1L;
    }
}