Midwinter Graces began as a suggestion by Doug Morris, chairman and chief executive officer of Universal Music Group, who, according to Amos, encouraged her to tackle and complete the project at a moment's notice, in March 2009.

After a summer of writing original material and rearranging established hymns and carols for the album, Amos, while still on the road for her 2009 world tour, began recording.

In early November 2009, Amos gave an interview for Pride Source Magazine, in which she disclosed the primary reasoning behind the album.

"[6] Amos, who has struggled with and fought her religious upbringing, both through her music and with her own mosaic set of beliefs, approached the prospect of doing a holiday album, or seasonal record, from the perspective of someone who was struggling to gain a deep and enriching spirituality not necessarily tied to a set of dogmatic beliefs: "I felt that as a minister’s daughter I could open up the circle to all those people who might not want to embrace Christianity, but have a spiritual feeling about the time.

[5] "The record contains a lot of story and beauty, and it does transcend some of the shame that gets attached to some of the music even during the season," noted Amos.

"[9] Due to Doug Morris' request being on such short notice, Amos found herself writing and recording the album on the road while on her 2009 world tour in support of Abnormally Attracted to Sin.

Recording sessions were held in Los Angeles, Chicago, New York City, Toronto and in Cornwall, England at various points during 2009.

[11] Independent music magazine, American Songwriter, called the album "Dark, piano-driven [and] spectacularly unique", crediting Amos with offering up something "gothic, inspired and winter-y.

"[13] Billboard noted, "Amos reaches deep into the world of carols for ancient and less obvious fare that she subsequently recasts on string-laden songs," praising the album, finally, as "a typically provocative-in the best possible way-entry in the yuletide canon.

"[14] The New York Times noted, "Gorgeously recorded and impeccably produced, [it's an album that] dwells in hymn-like serenity and diaphonous wonder.

"[23] The Guardian, which gave the album 4/5 stars, noted enthusiastically, "Centre stage is given to her voice and the simple arrangements," adding, "Amos sounds so tranquil she could almost be floating, but the stateliness of the orchestral backing keeps the songs grounded.

The first review was mixed, giving the album 3/5 stars and criticizing some of the song arrangements and production choices, though it did say, "The pluses outweigh the minuses [on this album], with further highlights coming courtesy of Amos' own 'Winter's Carol' and 'A Silent Night with You' – the former blessed with stately, hypnotic grace, while the latter's undulating melody evokes the warmth of a reverie triggered by seasonal radio fare.

"Stylistically," they continued, "with all the tootling flutes, arpeggiating harpsichords and sonorous electric violins, it's reminiscent of folk-rock bands circa the cusp of the 1970s."

They also noted, "Even when she is singing a "straight" rendition of a Christmas chestnut, there's always an underlying feeling that every syllable is laden with intrigue and layered with hidden meaning."

"[28] Drowned in Sound observed, "Fans of her earlier work will delight in the more direct, piano-driven melodies and orchestral arrangements that dominate the album, as well as the welcomed return of the long neglected harpsichord on several tracks,"[15] A mixed review by The Skinny called the album "moderately successful," awarding it 3/5 stars.

[29] Slant Magazine gave the album 3/5 stars, citing Winter's Carol, a song from and preview of Amos' upcoming musical adaptation of George MacDonald's The Light Princess, as the standout track: "The song's strong melody and arrangement are reminiscent of something from Under the Pink, bolstering a pagan yarn about the passing of the seasons."

"[21] Consequence of Sound gave it four stars out of five and called it "a pleasant and often gorgeous effort,"[30] and Internet magazine, PopMatters, cited the album as "Amos’ best work in years.

"[19] AllMusic was not impressed, however, giving it two-and-a-half stars out of five and stating, "Thanks to some familiar melodies, it can sometimes seem seasonally appropriate, but it always seems purely Tori, who has somehow managed to deliver an easy listening version of all her signatures in one tidy, not so-Christmasy, package.

"[12] The Huffington Post concluded, "Tori Amos’ beautiful vocals and recordings range between visions of an orphan looking at delicacies through frosty restaurant windows to dark stories from a worldly soul who's seen too many mirthless seasons pass.

In either case, whether she's turning around standard carols or adding her own titles to the secular Christmas catalog, Amos is so at home in this wintry environment, she may want to consider permanently keeping Spring at bay.

[36] On December 9, 2009, Amos also offered up two more official videos of solo-performances - "Star of Wonder" and "Jeanette, Isabella" - via social-networking sites such as Facebook, Twitter and MySpace.

[37] On December 18, 2009, ABC's Nightline did a short piece on Amos, focusing on her musical inspirations and her unique relationship with the piano.

[10] Entry to the concert required a wristband handed out at the HMV store at 150 Oxford Street starting at 8:00 AM on the day of the performance.

On December 8, 2009, Amos held a private invitation-only set in which a hundred or so music insiders and personnel gathered at Spin Magazine's office headquarters as part of their SPINHouse Live series.