When natural days are short, photoperiodic lighting at the end or beginning of the day (day extension) or in the middle of the night (night break) promotes flowering of long-day plants. The objective of this study was to compare broad-spectrum warm-white light-emitting diodes (LEDs) and red (R) + far-red (FR) LEDs at flowering regulation when delivered at different timings in the night period. We performed a greenhouse experiment on four long-day ornamentals [coreopsis (Coreopsis grandiflora) ‘Early Sunrise’, snapdragon (Antirrhinum majus) ‘Liberty Classic Yellow’, petunia (Petunia ×hybrida) ‘Easy Wave Burgundy Star’, and petunia ‘Wave Purple Improved’]. We grew plants under a truncated 8-hour photoperiod with or without low-intensity (∼2 μmol·m−2·s−1) nighttime lighting from warm-white or R+FR LEDs. For each light quality, we delivered four timings: 1) 8 hours after dusk; 2) 8 hours before dawn; 3) 4 hours after dusk + 4 hours before dawn; and 4) 4-hour night break. The effectiveness of floral promotion was determined by time from the treatment onset to the first open flower. Coreopsis flowered similarly under all lighting treatments, irrespective of light quality and timing, but did not flower under the short-day treatment by the end of the experiment. At flowering, coreopsis was 18% to 19% shorter under white than R+FR LEDs. In contrast, snapdragon flowered 9 to 20 days later under white than R+FR LEDs, when delivered for 8 hours at night, but flowered similarly under these two lamp types as a 4-hour night break. Compared with the short-day treatment, white and R+FR LEDs promoted flowering of both petunia cultivars, although flowering generally occurred later under white than R+FR LEDs. Snapdragon and petunia ‘Easy Wave Burgundy Star’ developed 30% to 122% more lateral branches under white than R+FR LEDs, when delivered for 8 hours at night. The effectiveness of warm-white LEDs was generally unaffected by timing, although it was most promotive of flowering in snapdragon when delivered for 8 hours before dawn. For R+FR LEDs, 8-hour day-extension lighting was generally more effective than 4-hour night-break lighting, irrespective of timing. We conclude when delivered for 8 hours at night, warm-white LEDs are generally less effective than R+FR LEDs at promoting flowering of long-day ornamentals but similarly effective as 4-hour night-break lighting. The effectiveness of day-extension lighting is generally independent of timing, although for R+FR LEDs, 8 hours after-dusk and/or before-dawn lighting was generally more effective than 4-hour night-break lighting.