Every night (and day) of Chanukah is a time of joy and celebration, but the fifth night holds a special place in many traditions, including Chabad. On this night, the rebbes would traditionally host family gatherings called “latke evenings.”1 It's also customary to give additional Chanukah gelt, more than on other nights.2

What is so special about this night? Here are a number of reasons for the extra celebratory atmosphere on the fifth night of Chanukah:

Never on Shabbat

Chanukah can start on any day of the week except for Monday. This scheduling means that the fifth night of Chanukah never falls on Friday night, which is Shabbat. So if you only give Chanukah gelt on one night, this would be the ideal time to do it, as handling money is not permitted on Shabbat.3

The Rebbe gives a deeper explanation. Chanukah is all about bringing light to the darkness, and since the 5th night always falls on a mundane weeknight, the darkness is especially thick and the light we bring is all that more powerful.4

We’ve Tipped the Scales!

The fifth night marks the first time more candles are lit than are left unlit, symbolizing a tipping point in bringing light into the world.5

This concept ties into a famous Talmudic debate between the School of Hillel and the School of Shammai. According to the School of Hillel, we should light one candle the first night and then add a candle each night (and this is the halachah that we follow). According to the School of Shammai, we light eight candles the first night and decrease by one candle each night.

The Rebbe explains that the Schools of Hillel and Shammai differ in their approaches to how we transform the darkness outside with the spiritual light of Chanukah.

The School of Shammai focuses on battling darkness. Thus, they advocate for a giant burst of light at the very start. Once that breakthrough occurs, subsequent battles require less intensity, and they decrease their candles accordingly.

The School of Hillel, however, prefers to increase goodness and allow evil to wither away on its own. They advocate consistently adding light, eventually influencing adversaries to willingly join the forces of light.

The fifth night is the first time when those following Hillel’s approach would have kindled more candles than their counterparts from Shammai’s House. This symbolizes the shift towards illuminating the entire darkness.6

Read: The Talmudic Debate on How to Change Your Life

It Is Yom Kippur Katan

The fifth day of Chanukah is the day before Rosh Chodesh Tevet.

The day before every Rosh Chodesh is known as Yom Kippur Katan (“Mini Yom Kippur”) and is a day of introspection and repentance for any wrongdoings during the past month.

It was once quite common for individuals or communities to fast and recite special Selichot prayers on this day. On this Yom Kippur Katan, however, these practices aren’t observed, in light of the joyous nature of Chanukah.7

Now, the Rebbe points out that it cannot be that Chanukah would cause us to miss out on any opportunities for repentance and spiritual growth.

Rather, on this Yom Kippur Katan, we can attain these spiritual highs without Tachanun in a joyful and celebratory way.8

Read: The Spiritual High of the Fifth Night

Freed from Prison (Again)

In Chabad circles, this day holds special historical significance:

In 1798, many chassidim who were incarcerated at the same time as the Alter Rebbe, Rabbi Shneur Zalman of Liadi, founder of Chabad, were released from prison. While he was freed on the 19th of Kislev, the chassidim were freed several days later, on the fifth day of Chanukah.

According to some, the Alter Rebbe himself was released from his second imprisonment (in 1800) on the fifth day of Chanukah (others say it was the third day of Chanukah). He was incarcerated because government scholars were concerned that certain elements emphasized and elaborated upon in his Chassidic philosophy might provoke defiance against the government. However, by clearly explaining his teachings and allaying their concerns, he secured his release.9