diff --git a/NAMESPACE b/NAMESPACE
index c0968e5c..9cc4a581 100644
--- a/NAMESPACE
+++ b/NAMESPACE
@@ -141,6 +141,7 @@ export(set_schedule_year)
 export(set_thumbnail)
 export(set_vanity_url)
 export(swap_vanity_url)
+export(swap_vanity_urls)
 export(tbl_connect)
 export(terminate_jobs)
 export(user_guid_from_username)
diff --git a/NEWS.md b/NEWS.md
index 02db3a14..e36f8644 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -10,10 +10,19 @@
   client with permissions scoped to the content visitor when running on a Connect
   server. (#362)
 
+## Enhancements and fixes
+
+- `swap_vanity_urls()` can correctly perform a swap involving a content item
+  with no vanity URL. (#360)
+- `swap_vanity_urls()` handles permissions errors gracefully, attempting to roll
+  back any changes made. (#360)
+
 ## Newly deprecated
 
 - `get_job()` (singular) is now deprecated, its functionality taken care of by
   other functions, including `get_log()`.
+- `swap_vanity_url(old, new)` has been deprecated and renamed to
+  `swap_vanity_urls(content_a, content_b)`.
 
 # connectapi 0.5.0
 
diff --git a/R/deploy.R b/R/deploy.R
index 796d6fed..120bbf5b 100644
--- a/R/deploy.R
+++ b/R/deploy.R
@@ -413,7 +413,7 @@ deploy_current <- function(content) {
 
 #' Set the Vanity URL
 #'
-#' Sets the Vanity URL for a piece of content.
+#' Set the vanity URL for a piece of content.
 #'
 #' @param content A Content object
 #' @param url The path component of the URL
@@ -453,7 +453,7 @@ set_vanity_url <- function(content, url, force = FALSE) {
 
 #' Delete the Vanity URL
 #'
-#' Deletes the Vanity URL for a piece of content.
+#' Delete the vanity URL for a piece of content.
 #'
 #' @param content A Content object
 #'
@@ -464,14 +464,14 @@ delete_vanity_url <- function(content) {
   error_if_less_than(con$version, "1.8.6")
   guid <- content$get_content()$guid
 
-  con$DELETE(v1_url("content", guid, "vanity"))
+  con$DELETE(v1_url("content", guid, "vanity"), parser = "parsed")
 
   content
 }
 
 #' Get the Vanity URL
 #'
-#' Gets the Vanity URL for a piece of content.
+#' Get the vanity URL for a piece of content.
 #'
 #' @param content A Content object
 #'
@@ -501,55 +501,80 @@ get_vanity_url <- function(content) {
   return(van$path)
 }
 
-#' Swap the Vanity URL
+#' Swap Vanity URLs
 #'
-#' Swaps the Vanity URLs between two pieces of content
+#' Swap the vanity URLs of two pieces of content.
 #'
-#' @param from_content A Content object
-#' @param to_content A Content object
+#' @param content_a A Content object
+#' @param content_b A Content object
+#'
+#' @returns A list of the new vanity URLs for `content_a` and `content_b`
 #'
 #' @family content functions
 #' @export
-swap_vanity_url <- function(from_content, to_content) {
-  warn_experimental("swap_vanity_url")
-  scoped_experimental_silence()
+swap_vanity_urls <- function(content_a, content_b) {
   # TODO: Add prompt if in an interactive session
   # TODO: Add pretty print output of what is happening
-  # TODO: Test error cases super thoroughly!!
-  # TODO: Do a "dry run" of sorts...? Check privileges... etc...
-  # TODO: Do the changes within a TryCatch so we can undo...?
-  # TODO: Need a way to "unset" a vanity URL
-
-  from_vanity <- get_vanity_url(from_content)
-  to_vanity <- get_vanity_url(to_content)
 
-  if (is.null(from_vanity) && is.null(to_vanity)) {
-    warning("Neither content has a Vanity URL. Exiting")
-  } else {
-    # swapping vanity URLs
-    tmp_vanity <- paste0("vanity-url-swap-", create_random_name(length = 50))
+  validate_R6_class(content_a, "Content")
+  validate_R6_class(content_b, "Content")
 
-    if (!is.null(from_vanity)) {
-      set_vanity_url(from_content, tmp_vanity)
-    } else {
-      set_vanity_url(to_content, tmp_vanity)
-    }
+  vanity_a <- get_vanity_url(content_a)
+  vanity_b <- get_vanity_url(content_b)
 
-    if (!is.null(from_vanity)) {
-      set_vanity_url(to_content, from_vanity)
+  if (is.null(vanity_a) && is.null(vanity_b)) {
+    warning("Neither content has a vanity URL")
+  } else {
+    tryCatch(
+      delete_vanity_url(content_a),
+      error = function(e) {
+        stop("Unable to modify the vanity URL for content_a: ", e$message, call. = FALSE)
+      }
+    )
+    tryCatch(
+      delete_vanity_url(content_b),
+      error = function(e) {
+        set_vanity_url(content_a, vanity_a)
+        stop("Unable to modify the vanity URL for content_b: ", e$message, call. = FALSE)
+      }
+    )
+    if (!is.null(vanity_a)) {
+      set_vanity_url(content_b, vanity_a)
     }
-    if (!is.null(to_vanity)) {
-      set_vanity_url(from_content, to_vanity)
+    if (!is.null(vanity_b)) {
+      set_vanity_url(content_a, vanity_b)
     }
-
-    from_vanity <- get_vanity_url(from_content)
-    to_vanity <- get_vanity_url(to_content)
+    vanity_a <- get_vanity_url(content_a)
+    vanity_b <- get_vanity_url(content_b)
   }
 
   return(
     list(
-      from = from_vanity,
-      to = to_vanity
+      content_a = vanity_a,
+      content_b = vanity_b
+    )
+  )
+}
+
+#' Swap Vanity URLs
+#'
+#' Swap the vanity URLs of two pieces of content.
+#' This function is deprecated; please use \code{\link{swap_vanity_urls}}.
+#'
+#' @param from A Content object
+#' @param to A Content object
+#'
+#' @returns A list of the new vanity URLs for `from` and `to`
+#'
+#' @family content functions
+#' @export
+swap_vanity_url <- function(from, to) {
+  lifecycle::deprecate_warn("0.6.0", "swap_vanity_url()", "swap_vanity_urls()")
+  res <- swap_vanity_urls(from, to)
+  return(
+    list(
+      from = res[["content_a"]],
+      to = res[["content_b"]]
     )
   )
 }
diff --git a/man/content_delete.Rd b/man/content_delete.Rd
index 7426166d..182d7226 100644
--- a/man/content_delete.Rd
+++ b/man/content_delete.Rd
@@ -45,6 +45,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/content_item.Rd b/man/content_item.Rd
index 79294792..ae0dda8b 100644
--- a/man/content_item.Rd
+++ b/man/content_item.Rd
@@ -51,6 +51,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/content_title.Rd b/man/content_title.Rd
index be347cd7..983c829e 100644
--- a/man/content_title.Rd
+++ b/man/content_title.Rd
@@ -47,6 +47,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/content_update.Rd b/man/content_update.Rd
index 8116acba..dfbad0b4 100644
--- a/man/content_update.Rd
+++ b/man/content_update.Rd
@@ -67,6 +67,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/create_random_name.Rd b/man/create_random_name.Rd
index b27cc387..b2c1a73b 100644
--- a/man/create_random_name.Rd
+++ b/man/create_random_name.Rd
@@ -44,6 +44,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/dashboard_url.Rd b/man/dashboard_url.Rd
index dcbccd92..dd768143 100644
--- a/man/dashboard_url.Rd
+++ b/man/dashboard_url.Rd
@@ -44,6 +44,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/dashboard_url_chr.Rd b/man/dashboard_url_chr.Rd
index 7a951bce..11b19037 100644
--- a/man/dashboard_url_chr.Rd
+++ b/man/dashboard_url_chr.Rd
@@ -47,6 +47,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/delete_thumbnail.Rd b/man/delete_thumbnail.Rd
index 444d8bba..db635a20 100644
--- a/man/delete_thumbnail.Rd
+++ b/man/delete_thumbnail.Rd
@@ -55,6 +55,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/delete_vanity_url.Rd b/man/delete_vanity_url.Rd
index 0d43f075..ac440c14 100644
--- a/man/delete_vanity_url.Rd
+++ b/man/delete_vanity_url.Rd
@@ -10,7 +10,7 @@ delete_vanity_url(content)
 \item{content}{A Content object}
 }
 \description{
-Deletes the Vanity URL for a piece of content.
+Delete the vanity URL for a piece of content.
 }
 \seealso{
 Other content functions: 
@@ -39,6 +39,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/deploy_repo.Rd b/man/deploy_repo.Rd
index 1b91da91..018fe807 100644
--- a/man/deploy_repo.Rd
+++ b/man/deploy_repo.Rd
@@ -82,6 +82,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/environment.Rd b/man/environment.Rd
index f6d493e5..c183d5e5 100644
--- a/man/environment.Rd
+++ b/man/environment.Rd
@@ -64,6 +64,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/get_bundles.Rd b/man/get_bundles.Rd
index 2dbbee8f..47cbb2cf 100644
--- a/man/get_bundles.Rd
+++ b/man/get_bundles.Rd
@@ -44,6 +44,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 
@@ -73,6 +74,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/get_image.Rd b/man/get_image.Rd
index cf270c40..b05e6b42 100644
--- a/man/get_image.Rd
+++ b/man/get_image.Rd
@@ -54,6 +54,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/get_job.Rd b/man/get_job.Rd
index 1ae6133c..ad8b7d0a 100644
--- a/man/get_job.Rd
+++ b/man/get_job.Rd
@@ -48,6 +48,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/get_jobs.Rd b/man/get_jobs.Rd
index 938b5e3c..2e9d1d30 100644
--- a/man/get_jobs.Rd
+++ b/man/get_jobs.Rd
@@ -121,6 +121,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/get_log.Rd b/man/get_log.Rd
index cdb8e3ca..84320076 100644
--- a/man/get_log.Rd
+++ b/man/get_log.Rd
@@ -70,6 +70,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/get_thumbnail.Rd b/man/get_thumbnail.Rd
index 2c1bb04d..ad895092 100644
--- a/man/get_thumbnail.Rd
+++ b/man/get_thumbnail.Rd
@@ -60,6 +60,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/get_vanity_url.Rd b/man/get_vanity_url.Rd
index 1b25ad40..7ffd1cee 100644
--- a/man/get_vanity_url.Rd
+++ b/man/get_vanity_url.Rd
@@ -13,7 +13,7 @@ get_vanity_url(content)
 A character string (or NULL if not defined)
 }
 \description{
-Gets the Vanity URL for a piece of content.
+Get the vanity URL for a piece of content.
 }
 \seealso{
 Other content functions: 
@@ -42,6 +42,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/git.Rd b/man/git.Rd
index b47ec108..c99786e5 100644
--- a/man/git.Rd
+++ b/man/git.Rd
@@ -67,6 +67,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/has_thumbnail.Rd b/man/has_thumbnail.Rd
index cd6cc995..129d7d77 100644
--- a/man/has_thumbnail.Rd
+++ b/man/has_thumbnail.Rd
@@ -56,6 +56,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/permissions.Rd b/man/permissions.Rd
index c0de1503..fbbee864 100644
--- a/man/permissions.Rd
+++ b/man/permissions.Rd
@@ -89,6 +89,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/set_image.Rd b/man/set_image.Rd
index 8b04cb20..4d9b6709 100644
--- a/man/set_image.Rd
+++ b/man/set_image.Rd
@@ -60,6 +60,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/set_run_as.Rd b/man/set_run_as.Rd
index c3b6a70a..40905d18 100644
--- a/man/set_run_as.Rd
+++ b/man/set_run_as.Rd
@@ -62,6 +62,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/set_thumbnail.Rd b/man/set_thumbnail.Rd
index d8060ef0..57b441fa 100644
--- a/man/set_thumbnail.Rd
+++ b/man/set_thumbnail.Rd
@@ -59,6 +59,7 @@ Other content functions:
 \code{\link{set_run_as}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/set_vanity_url.Rd b/man/set_vanity_url.Rd
index 4b43e264..e65a4265 100644
--- a/man/set_vanity_url.Rd
+++ b/man/set_vanity_url.Rd
@@ -17,7 +17,7 @@ set_vanity_url(content, url, force = FALSE)
 An updated Content object
 }
 \description{
-Sets the Vanity URL for a piece of content.
+Set the vanity URL for a piece of content.
 }
 \examples{
 \dontrun{
@@ -55,6 +55,7 @@ Other content functions:
 \code{\link{set_run_as}()},
 \code{\link{set_thumbnail}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/swap_vanity_url.Rd b/man/swap_vanity_url.Rd
index b4c2ea92..1d09db6b 100644
--- a/man/swap_vanity_url.Rd
+++ b/man/swap_vanity_url.Rd
@@ -2,17 +2,21 @@
 % Please edit documentation in R/deploy.R
 \name{swap_vanity_url}
 \alias{swap_vanity_url}
-\title{Swap the Vanity URL}
+\title{Swap Vanity URLs}
 \usage{
-swap_vanity_url(from_content, to_content)
+swap_vanity_url(from, to)
 }
 \arguments{
-\item{from_content}{A Content object}
+\item{from}{A Content object}
 
-\item{to_content}{A Content object}
+\item{to}{A Content object}
+}
+\value{
+A list of the new vanity URLs for \code{from} and \code{to}
 }
 \description{
-Swaps the Vanity URLs between two pieces of content
+Swap the vanity URLs of two pieces of content.
+This function is deprecated; please use \code{\link{swap_vanity_urls}}.
 }
 \seealso{
 Other content functions: 
@@ -41,6 +45,7 @@ Other content functions:
 \code{\link{set_run_as}()},
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()},
 \code{\link{verify_content_name}()}
 }
diff --git a/man/swap_vanity_urls.Rd b/man/swap_vanity_urls.Rd
new file mode 100644
index 00000000..93b78052
--- /dev/null
+++ b/man/swap_vanity_urls.Rd
@@ -0,0 +1,51 @@
+% Generated by roxygen2: do not edit by hand
+% Please edit documentation in R/deploy.R
+\name{swap_vanity_urls}
+\alias{swap_vanity_urls}
+\title{Swap Vanity URLs}
+\usage{
+swap_vanity_urls(content_a, content_b)
+}
+\arguments{
+\item{content_a}{A Content object}
+
+\item{content_b}{A Content object}
+}
+\value{
+A list of the new vanity URLs for \code{content_a} and \code{content_b}
+}
+\description{
+Swap the vanity URLs of two pieces of content.
+}
+\seealso{
+Other content functions: 
+\code{\link{content_delete}()},
+\code{\link{content_item}()},
+\code{\link{content_title}()},
+\code{\link{content_update}()},
+\code{\link{create_random_name}()},
+\code{\link{dashboard_url}()},
+\code{\link{dashboard_url_chr}()},
+\code{\link{delete_thumbnail}()},
+\code{\link{delete_vanity_url}()},
+\code{\link{deploy_repo}()},
+\code{\link{get_bundles}()},
+\code{\link{get_environment}()},
+\code{\link{get_image}()},
+\code{\link{get_job}()},
+\code{\link{get_jobs}()},
+\code{\link{get_log}()},
+\code{\link{get_thumbnail}()},
+\code{\link{get_vanity_url}()},
+\code{\link{git}},
+\code{\link{has_thumbnail}()},
+\code{\link{permissions}},
+\code{\link{set_image_path}()},
+\code{\link{set_run_as}()},
+\code{\link{set_thumbnail}()},
+\code{\link{set_vanity_url}()},
+\code{\link{swap_vanity_url}()},
+\code{\link{terminate_jobs}()},
+\code{\link{verify_content_name}()}
+}
+\concept{content functions}
diff --git a/man/terminate_jobs.Rd b/man/terminate_jobs.Rd
index 0ba9b6fb..6355a96f 100644
--- a/man/terminate_jobs.Rd
+++ b/man/terminate_jobs.Rd
@@ -73,6 +73,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{verify_content_name}()}
 }
 \concept{content functions}
diff --git a/man/verify_content_name.Rd b/man/verify_content_name.Rd
index 178c1b5c..b9c590e0 100644
--- a/man/verify_content_name.Rd
+++ b/man/verify_content_name.Rd
@@ -48,6 +48,7 @@ Other content functions:
 \code{\link{set_thumbnail}()},
 \code{\link{set_vanity_url}()},
 \code{\link{swap_vanity_url}()},
+\code{\link{swap_vanity_urls}()},
 \code{\link{terminate_jobs}()}
 }
 \concept{content functions}
diff --git a/tests/integrated/test-deploy.R b/tests/integrated/test-deploy.R
index 99ceb998..0a6881c2 100644
--- a/tests/integrated/test-deploy.R
+++ b/tests/integrated/test-deploy.R
@@ -352,42 +352,41 @@ test_that("delete_vanity_url works", {
   expect_null(res)
 })
 
-test_that("swap_vanity_url works", {
-  tmp_content_name <- uuid::UUIDgenerate()
-  tmp_content_prep <- content_ensure(test_conn_1, name = tmp_content_name)
-  tmp_content <- Content$new(connect = test_conn_1, content = tmp_content_prep)
+test_that("swap_vanity_urls works", {
+  tmp_content_a_name <- uuid::UUIDgenerate()
+  tmp_content_a_prep <- content_ensure(test_conn_1, name = tmp_content_a_name)
+  tmp_content_a <- Content$new(connect = test_conn_1, content = tmp_content_a_prep)
 
-  tmp_content2_name <- uuid::UUIDgenerate()
-  tmp_content2_prep <- content_ensure(test_conn_1, name = tmp_content2_name)
-  tmp_content2 <- Content$new(connect = test_conn_1, content = tmp_content2_prep)
+  tmp_content_b_name <- uuid::UUIDgenerate()
+  tmp_content_b_prep <- content_ensure(test_conn_1, name = tmp_content_b_name)
+  tmp_content_b <- Content$new(connect = test_conn_1, content = tmp_content_b_prep)
 
   # warns with no vanity urls
-  res <- suppressMessages(expect_warning(swap_vanity_url(tmp_content, tmp_content2)))
-  expect_null(res[["from"]])
-  expect_null(res[["to"]])
+  res <- suppressMessages(expect_warning(swap_vanity_urls(tmp_content_a, tmp_content_b)))
+  expect_null(res[["content_a"]])
+  expect_null(res[["content_b"]])
 
-  # works with just one vanity url (from)
-  set_from <- set_vanity_url(tmp_content, tmp_content_name)
-  swap_res <- suppressMessages(swap_vanity_url(tmp_content, tmp_content2))
+  # works with just one vanity url (content_a)
+  set_content_a <- set_vanity_url(tmp_content_a, tmp_content_a_name)
+  swap_res <- suppressMessages(swap_vanity_urls(tmp_content_a, tmp_content_b))
 
-  expect_identical(swap_res$to, paste0("/", tmp_content_name, "/"))
-  expect_true(grepl("vanity-url", swap_res$from))
+  expect_null(swap_res$content_a)
+  expect_identical(swap_res$content_b, paste0("/", tmp_content_a_name, "/"))
 
   # works with both vanity urls
-  swap_res2 <- suppressMessages(swap_vanity_url(tmp_content, tmp_content2))
+  swap_res2 <- suppressMessages(swap_vanity_urls(tmp_content_a, tmp_content_b))
 
-  expect_identical(swap_res2$from, paste0("/", tmp_content_name, "/"))
-  expect_identical(swap_res2$to, swap_res$from)
+  expect_identical(swap_res2$content_a, paste0("/", tmp_content_a_name, "/"))
+  expect_identical(swap_res2$content_b, swap_res$content_a)
 
-  # works with just one vanity url (to)
-  delete_vanity_url(tmp_content)
-  expect_null(get_vanity_url(tmp_content))
+  # works with just one vanity url (content_b)
+  delete_vanity_url(tmp_content_a)
+  expect_null(get_vanity_url(tmp_content_a))
 
-  swap_res3 <- swap_vanity_url(tmp_content, tmp_content2)
+  swap_res3 <- swap_vanity_urls(tmp_content_a, tmp_content_b)
 
-  expect_identical(swap_res3$from, swap_res$from)
-  expect_false(identical(swap_res3$to, swap_res2$from))
-  expect_true(grepl("vanity-url", swap_res3$to))
+  expect_identical(swap_res3$content_a, swap_res$content_a)
+  expect_null(swap_res3$content_b)
 })
 
 # misc functions ---------------------------------------------------
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/README.md b/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/README.md
new file mode 100644
index 00000000..259c1340
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/README.md
@@ -0,0 +1 @@
+This content item allows vanity URL operations.
\ No newline at end of file
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity-795fd3-PUT.json b/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity-795fd3-PUT.json
new file mode 100644
index 00000000..5afc6529
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity-795fd3-PUT.json
@@ -0,0 +1,5 @@
+{
+    "content_guid": "951bf3ad",
+    "path": "/95/",
+    "created_time": "2025-01-24T20:53:08Z"
+}
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity-DELETE.204 b/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity-DELETE.204
new file mode 100644
index 00000000..e69de29b
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity-babd80-PUT.json b/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity-babd80-PUT.json
new file mode 100644
index 00000000..d2065aba
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity-babd80-PUT.json
@@ -0,0 +1,5 @@
+{
+    "content_guid": "951bf3ad",
+    "path": "/new/",
+    "created_time": "2025-01-06T21:01:45Z"
+}
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity.json b/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity.json
new file mode 100644
index 00000000..f8a3eae8
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/951bf3ad/vanity.json
@@ -0,0 +1,5 @@
+{
+    "content_guid": "951bf3ad",
+    "path": "/95/",
+    "created_time": "2025-01-06T21:01:45Z"
+}
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b.json b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b.json
new file mode 100644
index 00000000..0db47904
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b.json
@@ -0,0 +1,49 @@
+// A content item that returns 403 errors when setting and deleting vanity URLs
+{
+    "guid": "c3426b0b",
+    "name": "most-used-dashboard-py",
+    "title": "Vanity URL Swap Test Blue",
+    "description": "",
+    "access_type": "acl",
+    "locked": false,
+    "locked_message": "",
+    "extension": false,
+    "connection_timeout": null,
+    "read_timeout": null,
+    "init_timeout": null,
+    "idle_timeout": null,
+    "max_processes": null,
+    "min_processes": null,
+    "max_conns_per_process": null,
+    "load_factor": null,
+    "memory_request": null,
+    "memory_limit": null,
+    "cpu_request": null,
+    "cpu_limit": null,
+    "amd_gpu_limit": null,
+    "nvidia_gpu_limit": null,
+    "service_account_name": null,
+    "default_image_name": null,
+    "created_time": "2024-07-12T20:52:06Z",
+    "last_deployed_time": "2024-07-12T20:52:08Z",
+    "bundle_id": "124935",
+    "app_mode": "quarto-static",
+    "content_category": "",
+    "parameterized": false,
+    "cluster_name": null,
+    "image_name": null,
+    "r_version": null,
+    "py_version": null,
+    "quarto_version": null,
+    "r_environment_management": null,
+    "default_r_environment_management": null,
+    "py_environment_management": null,
+    "default_py_environment_management": null,
+    "run_as": null,
+    "run_as_current_user": false,
+    "owner_guid": "fe07bf64",
+    "content_url": "https://connect.example/content/c3426b0b/",
+    "dashboard_url": "https://connect.example/connect/#/apps/c3426b0b",
+    "app_role": "viewer",
+    "id": "51871"
+}
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/README.md b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/README.md
new file mode 100644
index 00000000..7c6442bb
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/README.md
@@ -0,0 +1 @@
+This content item returns 403 errors when setting and deleting vanity URLs.
\ No newline at end of file
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity-4747c1-PUT.R b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity-4747c1-PUT.R
new file mode 100644
index 00000000..dc06cca5
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity-4747c1-PUT.R
@@ -0,0 +1,4 @@
+structure(list(
+  url = "__api__/v1/content/c3426b0b/vanity", status_code = 403L,
+  content = charToRaw("{\"code\":22,\"error\":\"You don't have permission to perform this operation.\",\"payload\":null}")
+), class = "response")
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity-DELETE.R b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity-DELETE.R
new file mode 100644
index 00000000..dc06cca5
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity-DELETE.R
@@ -0,0 +1,4 @@
+structure(list(
+  url = "__api__/v1/content/c3426b0b/vanity", status_code = 403L,
+  content = charToRaw("{\"code\":22,\"error\":\"You don't have permission to perform this operation.\",\"payload\":null}")
+), class = "response")
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity-babd80-PUT.R b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity-babd80-PUT.R
new file mode 100644
index 00000000..dc06cca5
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity-babd80-PUT.R
@@ -0,0 +1,4 @@
+structure(list(
+  url = "__api__/v1/content/c3426b0b/vanity", status_code = 403L,
+  content = charToRaw("{\"code\":22,\"error\":\"You don't have permission to perform this operation.\",\"payload\":null}")
+), class = "response")
diff --git a/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity.json b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity.json
new file mode 100644
index 00000000..6017f363
--- /dev/null
+++ b/tests/testthat/2024.08.0/__api__/v1/content/c3426b0b/vanity.json
@@ -0,0 +1,5 @@
+{
+    "content_guid": "c3426b0b",
+    "path": "/c3/",
+    "created_time": "2025-01-06T21:01:45Z"
+}
diff --git a/tests/testthat/test-deploy.R b/tests/testthat/test-deploy.R
index cda99c87..ff738842 100644
--- a/tests/testthat/test-deploy.R
+++ b/tests/testthat/test-deploy.R
@@ -65,3 +65,29 @@ test_that("bundle_dir errors for nonexistent paths", {
     "not TRUE"
   )
 })
+
+test_that("swap_vanity_urls() fails gracefully", {
+  with_mock_api({
+    client <- connect(server = "https://connect.example", api_key = "fake")
+
+    works <- content_item(client, "951bf3ad")
+    fails <- content_item(client, "c3426b0b")
+
+    expect_error(
+      swap_vanity_urls(fails, works),
+      paste(
+        "Unable to modify the vanity URL for content_a:",
+        "https://connect\\.example/__api__/v1/content/c3426b0b/vanity",
+        "request failed with Client error: \\(403\\) Forbidden"
+      )
+    )
+    expect_error(
+      swap_vanity_urls(works, fails),
+      paste(
+        "Unable to modify the vanity URL for content_b:",
+        "https://connect\\.example/__api__/v1/content/c3426b0b/vanity",
+        "request failed with Client error: \\(403\\) Forbidden"
+      )
+    )
+  })
+})