diff --git a/.github/workflows/test-cli-ui_oss.yml b/.github/workflows/test-cli-ui_oss.yml
index 4dbdc9c981..26911eda38 100644
--- a/.github/workflows/test-cli-ui_oss.yml
+++ b/.github/workflows/test-cli-ui_oss.yml
@@ -98,6 +98,7 @@ jobs:
           echo "vault version:"
           vault version
       - name: Run cli bats tests
+        timeout-minutes: 30
         run: |
           export VAULT_ADDR=http://127.0.0.1:8200
           export VAULT_TOKEN=boundarytok
diff --git a/internal/tests/cli/boundary/_connect.bash b/internal/tests/cli/boundary/_connect.bash
index bb0d4b5d34..8a15aa2e3a 100644
--- a/internal/tests/cli/boundary/_connect.bash
+++ b/internal/tests/cli/boundary/_connect.bash
@@ -4,18 +4,18 @@
 function connect_nc() {
   local id=$1
   # Note: When this command returns, the session immediately goes into a "canceling" state
-  echo "foo" | boundary connect -exec nc -target-id $id -- {{boundary.ip}} {{boundary.port}}
+  echo "SSH-2.0-Test" | boundary connect -exec nc -target-id $id -- -v -w 5 {{boundary.ip}} {{boundary.port}}
 }
 
 function connect_alias() {
   local alias=$1
   # Note: When this command returns, the session immediately goes into a "canceling" state
-  echo "foo" | boundary connect $alias -exec nc -- {{boundary.ip}} {{boundary.port}}
+  echo "SSH-2.0-Test" | boundary connect $alias -exec nc -- -v -w 5 {{boundary.ip}} {{boundary.port}}
 }
 
 function connect_alias_with_host_id() {
   local alias=$1
   local hostid=$2
   # Note: When this command returns, the session immediately goes into a "canceling" state
-  echo "foo" | boundary connect $alias -host-id $hostid -exec nc -- {{boundary.ip}} {{boundary.port}}
+  echo "SSH-2.0-Test" | boundary connect $alias -host-id $hostid -exec nc -- -v -w 5 {{boundary.ip}} {{boundary.port}}
 }