Return all regex matches even when there is partial overlap in the matches

I have a regex pattern that looks for multiple words in a text and returns the match + (up to) five words that precede the match and the five words that follow the match.

The problem is that if within this range of words the regex matches multiple terms, only the first match will be returned.
For example, the following regex essentially looks for the words "book" and "page"
and the \\b(?:\\W+\\w+){0,5} part before and behind the regex also includes the extra words.

The following example only returns a single match:

test_str <- "Made out of wood, a book can contain many pages that are used to transmit information."

my_regex <- "(?i)\\b(?:\\w+\\W+){0,5}(\\bbook?\\w+|\\bpage?\\w+)\\b(?:\\W+\\w+){0,5}"

stringr::str_extract_all(test_str, pattern = my_regex)


[[1]]
[1] "Made out of wood, a book can contain many pages that"

While I would expect:

[[1]]
[1] "Made out of wood, a **book** can contain many pages that"
[2] "a book can contain many **pages** that are used to transmit"

(Matches highlighted)

I tried to solve this by using a positive lookahead assertion but I did not get it to work as I wanted.
What can I do to modify my regex?

You could split the regex into several bits instead of using the or operator "|"

test_str <- "Made out of wood, a book can contain many pages that are used to transmit information."

lr <- list()
lr[1] <- "(?i)\\b(?:\\w+\\W+){0,5}(\\bbook?\\w+)\\b(?:\\W+\\w+){0,5}"
lr[2] <- "(?i)\\b(?:\\w+\\W+){0,5}(\\bpage?\\w+)\\b(?:\\W+\\w+){0,5}"

sapply(lr, function(x) stringr::str_extract_all(test_str, pattern = x))

[[1]]
[1] "Made out of wood, a book can contain many pages that"

[[2]]
[1] "a book can contain many pages that are used to transmit"

As shown in this answer, you can enclose what you want to capture in a positive lookahead pattern, and then replace match.length with the capture.length attribute to allow the otherwise zero-length match to actually cover what's captured.

A secondary problem arises when you use a lookahead pattern for captures because you want to match "up to" 5 words before and after a keyword, and every word within 5 words of the keyword can satisfy the assertion if you use only a simple quantifier like (?:\\w+\\W+){0,5}. Instead, since you only want to match less than 5 words before a keyword when the preceding words start from the beginning of a line, include ^(?:\\w+\\W+){0,4} as an alternation pattern. The same idea applies to matching "up to" 5 words that follow the keyword:

test_str <- "Made out of wood, a book can contain many pages that are used to transmit information."

my_regex <- "(?i)(?=(\\b(?:(?:\\w+\\W+){5}|^(?:\\w+\\W+){0,4})(?:\\bbooks?|\\bpages?)\\b(?:(?:\\W+\\w+){5}|(?:\\W+\\w+){0,4}$)))"

m <- gregexpr(my_regex, test_str, perl=TRUE)
m <- lapply(m, function(i) {
       attr(i, "match.length") <- attr(i, "capture.length")
       i
     })
regmatches(test_str, m)

Demo: https://ideone.com/wZPdd2