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 $hostid -exec nc -- -v -w 5 {{boundary.ip}} {{boundary.port}}
 }
diff --git a/internal/tests/cli/boundary/alias.bats b/internal/tests/cli/boundary/alias.bats
index 262d6aa9f4..600b60c32d 100644
--- a/internal/tests/cli/boundary/alias.bats
+++ b/internal/tests/cli/boundary/alias.bats
@@ -127,6 +127,8 @@ export NEW_HOST="host_for_alias_test"
 @test "boundary/alias: admin user cannot connect using an alias configured with host id passing in different host id" {
   local new_host_id=$(host_id NEW_HOST $DEFAULT_HOST_CATALOG)
   run connect_alias_with_host_id $ALIAS_VALUE $new_host_id
+  echo "connecting: $output"
+  echo "status: $status"
   [ "$status" -eq 1 ]
 }
 
diff --git a/internal/tests/cli/boundary/sessions.bats b/internal/tests/cli/boundary/sessions.bats
index e2f04c12de..1b056488e5 100644
--- a/internal/tests/cli/boundary/sessions.bats
+++ b/internal/tests/cli/boundary/sessions.bats
@@ -11,13 +11,13 @@ load _helpers
   [ "$status" -eq 0 ]
 
   run connect_nc $DEFAULT_TARGET
-  echo "connecting to $id: $output"
+  echo "connecting: $output"
   echo "status: $status"
   [ "$status" -eq 0 ]
 
   # Run twice so we have two values for later testing
   run connect_nc $DEFAULT_TARGET
-  echo "connecting to $id: $output"
+  echo "connecting: $output"
   echo "status: $status"
   [ "$status" -eq 0 ]
 }
@@ -28,13 +28,13 @@ load _helpers
   [ "$status" -eq 0 ]
 
   run connect_nc $DEFAULT_TARGET
-  echo "connecting to $id: $output"
+  echo "connecting: $output"
   echo "status: $status"
   [ "$status" -eq 0 ]
 
   # Run twice so we have two values for later testing
   run connect_nc $DEFAULT_TARGET
-  echo "connecting to $id: $output"
+  echo "connecting: $output"
   echo "status: $status"
   [ "$status" -eq 0 ]
 }
diff --git a/internal/tests/cli/boundary/target.bats b/internal/tests/cli/boundary/target.bats
index 559194be2a..febe5d4aac 100644
--- a/internal/tests/cli/boundary/target.bats
+++ b/internal/tests/cli/boundary/target.bats
@@ -14,6 +14,8 @@ load _target_host_sources
 
 @test "boundary/target/connect: admin user can connect to default target" {
   run connect_nc $DEFAULT_TARGET
+  echo "connecting: $output"
+  echo "status: $status"
   [ "$status" -eq 0 ]
 }
 
@@ -29,7 +31,7 @@ load _target_host_sources
 
 @test "boundary/target/connect: unpriv user can connect to default target" {
   run connect_nc $DEFAULT_TARGET
-  echo "connecting to $id: $output"
+  echo "connecting: $output"
   echo "status: $status"
   [ "$status" -eq 0 ]
 }
@@ -88,7 +90,7 @@ load _target_host_sources
 @test "boundary/target/connect: default user can connect to created target" {
   local id=$(target_id_from_name $DEFAULT_P_ID $TGT_NAME)
   run connect_nc $id
-  echo "connecting to $id: $output"
+  echo "connecting: $output"
   echo "status: $status"
   [ "$status" -eq 0 ]
 }
diff --git a/internal/tests/cli/boundary/target_aliases.bats b/internal/tests/cli/boundary/target_aliases.bats
index c2a152c634..26e3d55de4 100644
--- a/internal/tests/cli/boundary/target_aliases.bats
+++ b/internal/tests/cli/boundary/target_aliases.bats
@@ -23,6 +23,8 @@ export ALIAS_TGT_NAME='test-alias-target'
 
 @test "boundary/alias/target: admin user can connect to default target using alias" {
   run connect_alias $ALIAS_VALUE
+  echo "connecting: $output"
+  echo "status: $status"
   [ "$status" -eq 0 ]
 }
 
@@ -38,6 +40,8 @@ export ALIAS_TGT_NAME='test-alias-target'
 
 @test "boundary/alias/target: unpriv user can connect to default target" {
   run connect_alias $ALIAS_VALUE
+  echo "connecting: $output"
+  echo "status: $status"
   [ "$status" -eq 0 ]
 }
 
@@ -85,7 +89,8 @@ export ALIAS_TGT_NAME='test-alias-target'
 
 @test "boundary/alias/target: default user can connect to created target using alias" {
   run connect_alias $ALIAS_VALUE
-  echo "connecting to $ALIAS_VALUE: $output"
+  echo "connecting: $output"
+  echo "status: $status"
   [ "$status" -eq 0 ]
 }
 
@@ -136,4 +141,4 @@ export ALIAS_TGT_NAME='test-alias-target'
   run delete_alias $aid
   run has_status_code "$output" "204"
   [ "$status" -eq 0 ]
-}
\ No newline at end of file
+}