diff --git a/R/glue.R b/R/glue.R
index 3cc96688b..22ba1d069 100644
--- a/R/glue.R
+++ b/R/glue.R
@@ -130,8 +130,15 @@ collapse_head_notrim <- function(x, trunc, sep, sep2, last, ellipsis) {
 
   lnx <- length(x)
 
-  if (lnx == 1L) return(x)
-  if (lnx == 2L) return(paste0(x, collapse = sep2))
+  if (lnx == 1L)
+    return(x)
+  if (lnx == 2L) {
+    # Handle the case where last is changed and sep2 is not
+    if (sep2 == " and " & last != ", and ")
+      return(paste0(x, collapse = last))
+    else
+      return(paste0(x, collapse = sep2))
+  }
   if (lnx <= trunc) {
     # no truncation
     return(paste0(
diff --git a/tests/testthat/_snaps/collapsing.md b/tests/testthat/_snaps/collapsing.md
index 6d5583385..e9b5421f9 100644
--- a/tests/testthat/_snaps/collapsing.md
+++ b/tests/testthat/_snaps/collapsing.md
@@ -455,3 +455,22 @@
     Output
       [1] "a, b, c, d, e, f, g, h, i, and j"
 
+# Issue #681
+
+    Code
+      v <- cli::cli_vec(c("foo", "bar", "foobar"), style = list(`vec-last` = ", or "))
+      cli::cli_text("Must be one of: {v}.")
+    Message
+      Must be one of: foo, bar, or foobar.
+    Code
+      v <- cli::cli_vec(c("foo", "bar"), style = list(`vec-last` = " or "))
+      cli::cli_text("Must be one of: {v}.")
+    Message
+      Must be one of: foo or bar.
+    Code
+      v <- cli::cli_vec(c("foo", "bar"), style = list(`vec-last` = " or ",
+        `vec-sep2` = " xor "))
+      cli::cli_text("Must be one of: {v}.")
+    Message
+      Must be one of: foo xor bar.
+
diff --git a/tests/testthat/test-collapsing.R b/tests/testthat/test-collapsing.R
index 4923dcc3e..2a567cc5c 100644
--- a/tests/testthat/test-collapsing.R
+++ b/tests/testthat/test-collapsing.R
@@ -197,3 +197,30 @@ test_that("ansi_collapse uses `sep2` for length-two inputs", {
   expect_equal(ansi_collapse(1:2, trunc = 2, style = "head"),
                "1 and 2")
 })
+
+
+test_that("Issue #681", {
+  expect_equal(ansi_collapse(1:2, last = " or "), "1 or 2")
+  expect_equal(ansi_collapse(1:2, sep2 = " and ", last = " or "), "1 or 2")
+  expect_equal(ansi_collapse(1:2, sep2 = " xor ", last = " or "), "1 xor 2")
+
+  expect_snapshot({
+    v <- cli::cli_vec(
+      c("foo", "bar", "foobar"),
+      style = list("vec-last" = ", or ")
+    )
+    cli::cli_text("Must be one of: {v}.")
+
+    v <- cli::cli_vec(
+      c("foo", "bar"),
+      style = list("vec-last" = " or ")
+    )
+    cli::cli_text("Must be one of: {v}.")
+
+    v <- cli::cli_vec(
+      c("foo", "bar"),
+      style = list("vec-last" = " or ", "vec-sep2" = " xor ")
+    )
+    cli::cli_text("Must be one of: {v}.")
+  })
+})