Importance in Islam

“A prayer performed after using the miswak is better than seventy prayers without using it.”
Source: Ibn Majah (Sunan Ibn Majah), Hadith 288 — Classified as Hasan by some scholars.
Also narrated in Ibn Hibban, Ibn Khuzaimah, and al-Tabarani with slight variations.

Jabrael alaihis-salam recommended using a miswak so much that I feared that it would be made obligatory [fard].)
Source: Sunan Ibn Majah, Book of Purification, Hadith 289 — Classified as Sahih.

If I had not found it a hardship for my Ummah, I would order them to make wudu’ for every salat and to use miswak in every wudu. Sources:

Sahih al-Bukhari, Hadith 887
Sahih Muslim, Hadith 252
Sunan Abu Dawood, Hadith 41

Others Hadith

When you get up for Salat al-Layl, cleanse your mouth with a miswak, because an angel comes close to the mouth of the person reciting the Qur’an and listens to the recitation.” Source: Al-Daylami, Musnad al-Firdaws — This narration is reported with a weaker chain, but used in classical literature to emphasize etiquette.

Aishah (RA) on the Prophet’s Frequent Use of Miswak
“Whenever the Prophet (ﷺ) got up at night, he would clean his mouth with a miswak.”
Sources:

Sahih al-Bukhari, Hadith 245
Sahih Muslim, Hadith 255
Sunan Abu Dawood, Hadith 58

Also

“Verily, the Messenger of Allah sw would use the miswak before making wudu whenever he woke from sleep — whether it was night or day.” Source: Abu Dawood (similar hadiths in Bukhari & Muslim)

Imam Ghazali (R), in his Ihya-ul-Uloom, has discussed ten Aadaab (Respects or duties) of sleep. The very first of these being purity and the use of the Miswaak (before sleeping).
Allamah Sha’rani (R) states in the Kitaab, Kashful Ghummah, that Prophet Muhammad (Sallallahu Alayhi Wasallam): advised: “Whenever you retire for sleep, use the Miswaak.”
Ibn Umar (R) says that many a time Rasulullah used the Miswaak as much as four times in a single night. Hadhrat Aishah (R) narrates: “Verily, the Messenger of Allah (Sallallahu Alayhi Wasallam) would use the Miswaak before making Wudhu (ablutions) whenever he arose from sleep, whether it be during the night or during the day.” [ABU DAWOOD]
Imam Ghazali (Radhi Allahu Anhu) has mentioned in his Ihya-ul-Uloom that a person before sleeping at night should keep his water and Miswaak ready and close at hand. As soon as he wakes from sleep during the night he should immediately use the water and the Miswaak, and engage in the remembrance of Allah.

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