Welcome to the PLCTalk Forum community. I like your username, I have family and friends who went to ND Maryland, if that's the reference.
One reason that a similar rung would not turn on that bit is that the .EN and .DN output bits are mutually exclusive. Once a Timer is Done, the Enable bit turns off.
The other reason is that a timer always requires at least two scans of the PLC program to complete.
On every scan after the Timer is enabled, the operating system compares the elapsed number of CPU clock cycles to the Preset in milliseconds. If the accumulated time is equal to or greater than the preset, the .DN bit is set.
But if the Preset is zero, the operating system doesn't evaluate the accumulated time instantaneously and set the .DN bit on the very next instruction.
Because your sequencer increments the Sequence Step on the very next rung, the Timer is disabled on the next scan, and never compares its accumulated cycles to the Preset.