This series includes five decades of frequent and lengthy correspondence between second-generation Abstract Expressionist painter Helen Frankenthaler (1928-2011) and Sonya Rudikoff. Letters are primarily from Frankenthaler to Rudikoff, numbering around 234 letters and 314 postcards from 1950 to 1997, including several letters addressed to Robert Gutman and the Gutman family after Rudikoff's death. Also present are a few letters addressed to Rudikoff from Frankenthaler's husband, the prominent first-generation Abstract Expressionist painter Robert Motherwell (1915–1991) and his daughters. Motherwell also often signed and wrote postscripts to some of Frankenthaler's postcards throughout the 1960s.

This series includes Rudikoff's personal and professional correspondence from 1949 through 1997, along with some related correspondence of her husband, Robert Gutman, following her death in 1997. The original groups into which correspondence was filed were preserved and are reflected in the three file groups within this series, which include two distinct alphabetical runs of correspondence, divided by function into editorial and personal correspondence, along with a group of Robert Gutman's correspondence, both with Rudikoff throughout their courtship and marriage, as well as his correspondence regarding Rudikoff and her work, after her death.

This series primarily contains Rudikoff's notebooks, papers, diaries, planners, assessments, clippings, and coursework from her time at Bennington College from 1945 until her graduation in 1948. Composition notebooks contain extensive notes on her Bennington classes in literature, creative writing, art, logic, Greek, and psychology, the margins of which are usually lushly decorated with small sketches and doodles. Intimate diaries describe Rudikoff's experience as a young female college student in the late 1940s. Rudikoff's academic writings demonstrate an early interest in modernist women writers and include several drafts of her senior project, titled "Gertrude Stein's Blue Guitar: Studies in Language, Form, Motif."

This series contains writings and papers of Sonya Rudikoff, primarily unpublished works, including lectures and academic papers, often about Virginia Woolf, that Rudikoff presented at various conferences on Victorian literature, as well as typescripts of short stories and other fictional works. Of note is a typescript for a novel that portrays the life of a female Abstract Expressionist painter living in New York City in the late 1940s and early 1950s, possibly inspired by Rudikoff's roommate, Helen Frankenthaler. Although the typescript for the novel is untitled, an attached synopsis lists "Abstract Expressionism" and "Sybil, What Do You Want?" as possible titles. A curriculum vitae and bibliography of Rudikoff's published works is also included, documenting her frequent publications from the 1950s through the 1990s, which consist of literary reviews and essays appearing in major journals, including regular articles in The Hudson Review.