diff --git a/scripts/release.sh b/scripts/release.sh
index f35a1bfc8e..e5f950ebce 100755
--- a/scripts/release.sh
+++ b/scripts/release.sh
@@ -53,6 +53,10 @@ script_check=1
 mainline=1
 channel=mainline
 
+# These values will be used for any PRs created.
+pr_review_assignee=${CODER_RELEASE_PR_REVIEW_ASSIGNEE:-@me}
+pr_review_reviewer=${CODER_RELEASE_PR_REVIEW_REVIEWER:-bpmct,stirby}
+
 args="$(getopt -o h -l dry-run,help,ref:,mainline,stable,major,minor,patch,force,ignore-script-out-of-date -- "$@")"
 eval set -- "$args"
 while true; do
@@ -294,7 +298,7 @@ log "Release tags for ${new_version} created successfully and pushed to ${remote
 
 log
 # Write to a tmp file for ease of debugging.
-release_json_file=$(mktemp -t coder-release.json)
+release_json_file=$(mktemp -t coder-release.json.XXXXXX)
 log "Writing release JSON to ${release_json_file}"
 jq -n \
 	--argjson dry_run "${dry_run}" \
@@ -310,6 +314,49 @@ maybedryrun "${dry_run}" cat "${release_json_file}" |
 log
 log "Release workflow started successfully!"
 
+log
+log "Would you like for me to create a pull request for you to automatically bump the version numbers in the docs?"
+while [[ ! ${create_pr:-} =~ ^[YyNn]$ ]]; do
+	read -p "Create PR? (y/n) " -n 1 -r create_pr
+	log
+done
+if [[ ${create_pr} =~ ^[Yy]$ ]]; then
+	pr_branch=autoversion/${new_version}
+	title="docs: bump ${channel} version to ${new_version}"
+	body="This PR was automatically created by the [release script](https://github.com/coder/coder/blob/main/scripts/release.sh).
+
+Please review the changes and merge if they look good and the release is complete.
+
+You can follow the release progress [here](https://github.com/coder/coder/actions/workflows/release.yaml) and view the published release [here](https://github.com/coder/coder/releases/tag/${new_version}) (once complete)."
+
+	log
+	log "Creating branch \"${pr_branch}\" and updating versions..."
+
+	create_pr_stash=0
+	if ! git diff --quiet --exit-code -- docs; then
+		maybedryrun "${dry_run}" git stash push --message "scripts/release.sh: autostash (autoversion)" -- docs
+		create_pr_stash=1
+	fi
+	maybedryrun "${dry_run}" git checkout -b "${pr_branch}" "${remote}/${branch}"
+	execrelative go run ./release autoversion --channel "${channel}" "${new_version}" --dry-run
+	maybedryrun "${dry_run}" git add docs
+	maybedryrun "${dry_run}" git commit -m "${title}"
+	# Return to previous branch.
+	maybedryrun "${dry_run}" git checkout -
+	if ((create_pr_stash)); then
+		maybedryrun "${dry_run}" git stash pop
+	fi
+
+	log "Creating pull request..."
+	maybedryrun "${dry_run}" gh pr create \
+		--assignee "${pr_review_assignee}" \
+		--reviewer "${pr_review_reviewer}" \
+		--base "${branch}" \
+		--head "${pr_branch}" \
+		--title "${title}" \
+		--body "${body}"
+fi
+
 if ((dry_run)); then
 	# We can't watch the release.yaml workflow if we're in dry-run mode.
 	exit 0
diff --git a/scripts/release/main.go b/scripts/release/main.go
index 79580eee61..919205b76d 100644
--- a/scripts/release/main.go
+++ b/scripts/release/main.go
@@ -381,12 +381,18 @@ func (r *releaseCommand) autoversionFile(ctx context.Context, file, channel, ver
 			}
 		}
 		if matchRe != nil {
-			// Apply matchRe and find the group named "version", then replace it with the new version.
-			// Utilize the index where the match was found to replace the correct part. The only
-			// match group is the version.
+			// Apply matchRe and find the group named "version", then replace it
+			// with the new version.
 			if match := matchRe.FindStringSubmatchIndex(line); match != nil {
-				logger.Info(ctx, "updating version number", "line_number", i+1, "match", match)
-				lines[i] = line[:match[2]] + version + line[match[3]:]
+				vg := matchRe.SubexpIndex("version")
+				if vg == -1 {
+					logger.Error(ctx, "version group not found in match", "num_subexp", matchRe.NumSubexp(), "subexp_names", matchRe.SubexpNames(), "match", match)
+					return xerrors.Errorf("bug: version group not found in match")
+				}
+				start := match[vg*2]
+				end := match[vg*2+1]
+				logger.Info(ctx, "updating version number", "line_number", i+1, "match_start", start, "match_end", end, "old_version", line[start:end])
+				lines[i] = line[:start] + version + line[end:]
 				matchRe = nil
 				break
 			}
diff --git a/scripts/release/tag_version.sh b/scripts/release/tag_version.sh
index 89fb738f8a..16a2011016 100755
--- a/scripts/release/tag_version.sh
+++ b/scripts/release/tag_version.sh
@@ -191,7 +191,7 @@ fi
 
 # Ensure the ref is in the release branch.
 branch_contains_ref=$(git branch --contains "${ref}" --list "${release_branch}" --format='%(refname)')
-if [[ -z $branch_contains_ref ]]; then
+if ((!dry_run)) && [[ -z $branch_contains_ref ]]; then
 	error "Provided ref (${ref_name}) is not in the required release branch (${release_branch})."
 fi
 
diff --git a/scripts/release/testdata/autoversion/docs/random.md b/scripts/release/testdata/autoversion/docs/random.md
new file mode 100644
index 0000000000..cfaf4c6d48
--- /dev/null
+++ b/scripts/release/testdata/autoversion/docs/random.md
@@ -0,0 +1,14 @@
+# Some documentation
+
+1. Run the following command to install the chart in your cluster.
+
+   For the **mainline** Coder release:
+
+   <!-- autoversion(mainline): "--version [version] # trailing comment!" -->
+
+   ```shell
+   helm install coder coder-v2/coder \
+       --namespace coder \
+       --values values.yaml \
+       --version 2.10.0 # trailing comment!
+   ```
diff --git a/scripts/release/testdata/autoversion/docs/random.md.golden b/scripts/release/testdata/autoversion/docs/random.md.golden
new file mode 100644
index 0000000000..9b62597ec3
--- /dev/null
+++ b/scripts/release/testdata/autoversion/docs/random.md.golden
@@ -0,0 +1,14 @@
+# Some documentation
+
+1. Run the following command to install the chart in your cluster.
+
+   For the **mainline** Coder release:
+
+   <!-- autoversion(mainline): "--version [version] # trailing comment!" -->
+
+   ```shell
+   helm install coder coder-v2/coder \
+       --namespace coder \
+       --values values.yaml \
+       --version 2.11.1 # trailing comment!
+   ```