diff --git a/managed/devops/opscli/ybops/cloud/common/ansible.py b/managed/devops/opscli/ybops/cloud/common/ansible.py
index adbfc530d50e..f806a45ff46c 100644
--- a/managed/devops/opscli/ybops/cloud/common/ansible.py
+++ b/managed/devops/opscli/ybops/cloud/common/ansible.py
@@ -267,6 +267,7 @@ def run(self, filename, extra_vars=None, host_info=None, print_output=True,
             stdout_str = stdout.decode('utf-8')
             stderr_str = stderr.decode('utf-8') if rc != 0 else ""
         if print_output:
+            # Write output to stderr by default.
             logging.info(stdout_str)
 
         if rc != 0:
diff --git a/managed/src/main/java/com/yugabyte/yw/common/ShellProcessHandler.java b/managed/src/main/java/com/yugabyte/yw/common/ShellProcessHandler.java
index 4aaf0247f8a1..471f076d241d 100644
--- a/managed/src/main/java/com/yugabyte/yw/common/ShellProcessHandler.java
+++ b/managed/src/main/java/com/yugabyte/yw/common/ShellProcessHandler.java
@@ -54,10 +54,10 @@ public class ShellProcessHandler {
 
   static final Pattern ANSIBLE_FAIL_PAT =
       Pattern.compile(
-          "(ybops.common.exceptions.YBOpsRuntimeError: Runtime error: "
-              + "Playbook run.* )with args.* (failed with.*? [0-9]+)");
+          "(ybops\\.common\\.exceptions\\.YB[^\\s]+Error:.*? Playbook run.*?)with args.* (failed"
+              + " with.*? [0-9]+)");
   static final Pattern ANSIBLE_FAILED_TASK_PAT =
-      Pattern.compile("TASK.*?fatal.*?FAILED.*", Pattern.DOTALL);
+      Pattern.compile("TASK\\s+\\[.+\\].*?(fatal:.*?FAILED.*|failed: (?!false).*)", Pattern.DOTALL);
   static final Pattern PYTHON_ERROR_PAT =
       Pattern.compile("(<yb-python-error>)(.*?)(</yb-python-error>)", Pattern.DOTALL);
   static final String ANSIBLE_IGNORING = "ignoring";
@@ -178,11 +178,12 @@ public ShellResponse run(List<String> command, ShellProcessContext context) {
               itse);
         }
         response.message = (response.code == ERROR_CODE_SUCCESS) ? processOutput : processError;
-        String specificErrMsg = getAnsibleErrMsg(response.code, processOutput, processError);
-        if (specificErrMsg == null) {
-          specificErrMsg = getPythonErrMsg(response.code, processOutput);
-        }
+        String specificErrMsg = getPythonErrMsg(response.code, processOutput);
         if (specificErrMsg != null) {
+          String ansibleErrMsg = getAnsibleErrMsg(response.code, specificErrMsg, processError);
+          if (ansibleErrMsg != null) {
+            specificErrMsg = ansibleErrMsg;
+          }
           response.message = specificErrMsg;
         }
       }
@@ -390,20 +391,21 @@ private static void destroyForcibly(Process process, String description) {
     }
   }
 
-  private static String getAnsibleErrMsg(int code, String stdout, String stderr) {
+  private static String getAnsibleErrMsg(int code, String pythonErrMsg, String stderr) {
 
-    if (stderr == null || code == ERROR_CODE_SUCCESS) return null;
+    if (pythonErrMsg == null || stderr == null || code == ERROR_CODE_SUCCESS) return null;
 
     String result = null;
 
-    Matcher ansibleFailMatch = ANSIBLE_FAIL_PAT.matcher(stderr);
+    Matcher ansibleFailMatch = ANSIBLE_FAIL_PAT.matcher(pythonErrMsg);
     if (ansibleFailMatch.find()) {
       result = ansibleFailMatch.group(1) + ansibleFailMatch.group(2);
 
-      // Attempt to find a line in ansible stdout for the failed task.
+      // By default, python logging module writes to stderr.
+      // Attempt to find a line in ansible stderr for the failed task.
       // Logs for each task are separated by empty lines.
-      // Some fatal failures are ignored by ansible, so skip them
-      for (String s : stdout.split("\\R\\R")) {
+      // Some fatal failures are ignored by ansible, so skip them.
+      for (String s : stderr.split("\\R\\R")) {
         if (s.contains(ANSIBLE_IGNORING)) {
           continue;
         }