diff --git a/R/upkeep.R b/R/upkeep.R
index ac7f17546..8d44be623 100644
--- a/R/upkeep.R
+++ b/R/upkeep.R
@@ -180,7 +180,8 @@ tidy_upkeep_checklist <- function(year = NULL,
       "### 2023",
       "",
       todo(
-        "Update email addresses *@rstudio.com -> *@posit.co",
+        "
+        Update email addresses *@rstudio.com -> *@posit.co",
         author_has_rstudio_email()
       ),
       todo(
@@ -213,11 +214,11 @@ tidy_upkeep_checklist <- function(year = NULL,
       todo("
         Consider running `use_tidy_dependencies()` and/or \\
         replace compat files with `use_standalone()`"),
-      todo("Use cli errors or file issue if you don\'t have time to do it now"),
+      todo("Use cli errors or [file an issue](new) if you don\'t have time to do it now"),
       todo('
         `use_standalone("r-lib/rlang", "types-check")` \\
         instead of home grown argument checkers;
-        or file issue if you don\'t have time to do it now'),
+        or [file an issue](new) if you don\'t have time to do it now'),
       todo(
         "
         Change files ending in `.r` to `.R` in R/ and/or tests/testthat/",
diff --git a/tests/testthat/_snaps/upkeep.md b/tests/testthat/_snaps/upkeep.md
index d2d1c05e6..7b6ba1bb7 100644
--- a/tests/testthat/_snaps/upkeep.md
+++ b/tests/testthat/_snaps/upkeep.md
@@ -41,9 +41,9 @@
       * [ ] `usethis::use_tidy_coc()`
       * [ ] Use `pak::pak("org/pkg")` in README
       * [ ] Consider running `use_tidy_dependencies()` and/or replace compat files with `use_standalone()`
-      * [ ] Use cli errors or file issue if you don't have time to do it now
+      * [ ] Use cli errors or [file an issue](new) if you don't have time to do it now
       * [ ] `use_standalone("r-lib/rlang", "types-check")` instead of home grown argument checkers;
-      or file issue if you don't have time to do it now
+      or [file an issue](new) if you don't have time to do it now
       * [ ] Add alt-text to pictures, plots, etc; see https://posit.co/blog/knitr-fig-alt/ for examples
       
       ### Eternal