diff --git a/internal/tests/cli/boundary/_connect.bash b/internal/tests/cli/boundary/_connect.bash
index 8a15aa2e3a..7db1b82d9a 100644
--- a/internal/tests/cli/boundary/_connect.bash
+++ b/internal/tests/cli/boundary/_connect.bash
@@ -4,18 +4,48 @@
 function connect_nc() {
   local id=$1
   # Note: When this command returns, the session immediately goes into a "canceling" state
-  echo "SSH-2.0-Test" | boundary connect -exec nc -target-id $id -- -v -w 5 {{boundary.ip}} {{boundary.port}}
+  # Capture output and check for success message since nc may return non-zero on pipe close
+  local output
+  output=$(echo "SSH-2.0-Test" | boundary connect -exec nc -target-id $id -- -v -w 5 {{boundary.ip}} {{boundary.port}} 2>&1)
+  local status=$?
+  echo "$output"
+
+  # If connection succeeded, return 0 regardless of nc's exit status
+  if echo "$output" | grep -q "succeeded"; then
+    return 0
+  fi
+  return $status
 }
 
 function connect_alias() {
   local alias=$1
   # Note: When this command returns, the session immediately goes into a "canceling" state
-  echo "SSH-2.0-Test" | boundary connect $alias -exec nc -- -v -w 5 {{boundary.ip}} {{boundary.port}}
+  # Capture output and check for success message since nc may return non-zero on pipe close
+  local output
+  output=$(echo "SSH-2.0-Test" | boundary connect $alias -exec nc -- -v -w 5 {{boundary.ip}} {{boundary.port}} 2>&1)
+  local status=$?
+  echo "$output"
+
+  # If connection succeeded, return 0 regardless of nc's exit status
+  if echo "$output" | grep -q "succeeded"; then
+    return 0
+  fi
+  return $status
 }
 
 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 "SSH-2.0-Test" | boundary connect $alias -host-id $hostid -exec nc -- -v -w 5 {{boundary.ip}} {{boundary.port}}
+  # Capture output and check for success message since nc may return non-zero on pipe close
+  local output
+  output=$(echo "SSH-2.0-Test" | boundary connect $alias -host-id $hostid -exec nc -- -v -w 5 {{boundary.ip}} {{boundary.port}} 2>&1)
+  local status=$?
+  echo "$output"
+
+  # If connection succeeded, return 0 regardless of nc's exit status
+  if echo "$output" | grep -q "succeeded"; then
+    return 0
+  fi
+  return $status
 }