[2] The establishment was successful and its earliest issues featured a host of South Asian Anglophone writers — Pankaj Mishra, Arundhati Roy, and Fatima Bhutto among others.

[2] Gradually, both Nath and Jose planned to cover stories that were ignored by mainstream media — Siddhartha Deb notes the magazine to have simultaneously carried traits of being a newsweekly, book review forum, and a litzine, during those days.

[2] Jose's profile of Narendra Modi in the March 2012 issue won international acclaim and was referenced by The Washington Post, The Wall Street Journal, The Guardian, Le Monde, and The New York Times.

[2] Dexter Filkins, writing for The New Yorker in 2019, noted that The Caravan provided generally critical coverage of the incumbent Bharatiya Janata Party government, notwithstanding state intimidation.

[7][8] In 2011, Jose won a Ramnath Goenka Award for his profiles of Prime Minister Manmohan Singh and DMK patriarch M. Karunanidhi;[9] two years later, he was conferred with the Osborn Elliott Prize by the Asia Society for two articles — one on the rebranding of Narendra Modi after the Gujarat Riots, and the other on media ethics.

[12] In 2021, Sagar won Red Ink Award in the category of crime reporting for his fact-checking of claims made by Central Bureau of Investigation in the context of Muzaffarpur shelter case.

[2] In 2011, the magazine was the subject of a Rs 50 crore defamation suit by the Indian Institute of Planning and Management after it featured a profile of its head, Arindam Chaudhuri.

[16][17] The magazine was issued legal notices in April 2013 regarding its May cover story about Attorney General Goolam Essaji Vahanvati but the top three editors decided to continue with its publication.

[30] In March 2023, The Caravan was accused of plagiarism after Netherlands-based artist Tijana claimed her artwork of featuring External Affairs Minister, S. Jaishankar was used on the magazine’s cover without permission.

[32][33] In 2019, following the Pulwama attack, The Caravan published an article analyzing the caste composition of the 40 personnel killed, noting that most were from OBC, SC, and ST backgrounds with limited upper-caste representation.

[34] The article drew sharp criticism from figures including CRPF’s chief spokesperson, Moses Dhinakaran, who called it “divisive,” and Union Minister Rajnath Singh, who emphasized that forces should not be viewed through caste or religious lines.

Former Jammu and Kashmir Chief Minister Mehbooba Mufti and others echoed similar concerns, while some defended the article, citing ongoing caste influences in the armed forces.