Whether with or from should be capitalized in a title or headline primarily depends the style guide you are using and the position of with or from in the title.
In AMA, AP, APA, and New York Times style, with or from is always capitalized, because these styles capitalize all prepositions with four or more letters.
Playing With Fire
Far From Home
In both Chicago and MLA style, all prepositions are lowercased, independent of their length, while in Bluebook and Wikipedia style, all prepositions with four or fewer letters are lowercased.
Coping with the Past
Escape from Home
However, with or from must still be capitalized if it is the first word of the title.
With Great Power Comes Great Responsibility
From Here to There
In Chicago, MLA, and Wikipedia style, the last word is also always capitalized.
A Force to Be Reckoned With
Things to run From
Bluebook style however does not have such a rule, so with or from remains lowercase when it is the last word.
Clients We Have Worked with
Things we run from
The rules for capitalizing with or from are as follows:
Do not capitalize with or from if …
- you are using sentence case and it is not the first word of the title
- you are using Chicago, MLA, or Wikipedia style title case and it is neither the first nor the last word
- you are using Bluebook style and it is not the first word
Capitalize with or from in all other cases.