diff --git a/src/Microsoft.SqlTools.ServiceLayer/Connection/ConnectionService.cs b/src/Microsoft.SqlTools.ServiceLayer/Connection/ConnectionService.cs
index d485ca97..b0fa53b0 100644
--- a/src/Microsoft.SqlTools.ServiceLayer/Connection/ConnectionService.cs
+++ b/src/Microsoft.SqlTools.ServiceLayer/Connection/ConnectionService.cs
@@ -22,7 +22,6 @@ using Microsoft.SqlTools.ServiceLayer.LanguageServices.Contracts;
 using Microsoft.SqlTools.ServiceLayer.Utility;
 using Microsoft.SqlTools.Utility;
 using System.Diagnostics;
-using System.Text.RegularExpressions;
 
 namespace Microsoft.SqlTools.ServiceLayer.Connection
 {
@@ -38,6 +37,12 @@ namespace Microsoft.SqlTools.ServiceLayer.Connection
 
         public const int MaxServerlessReconnectTries = 5; // Max number of tries to wait for a serverless database to start up when its paused before giving up.
 
+        // SQL Error Code Constants
+        // Referenced from: https://learn.microsoft.com/en-us/sql/relational-databases/errors-events/database-engine-events-and-errors?view=sql-server-ver16
+        private const int DoesNotMeetPWReqs = 18466; // Password does not meet complexity requirements.
+        private const int PWCannotBeUsed = 18463; // Password cannot be used at this time.
+
+
         /// <summary>
         /// Singleton service instance
         /// </summary>
@@ -1159,18 +1164,25 @@ namespace Microsoft.SqlTools.ServiceLayer.Connection
             catch (Exception ex)
             {
                 newResponse.Result = false;
-                newResponse.ErrorMessage = ex.InnerException != null ? (ex.Message + Environment.NewLine + Environment.NewLine + ex.InnerException.Message) : ex.Message;
-                newResponse.ErrorMessage = Regex.Replace(newResponse.ErrorMessage, @"\r?\nChanged database context to '\w+'\.", "");
-                newResponse.ErrorMessage = Regex.Replace(newResponse.ErrorMessage, @"\r?\nChanged language setting to \w+\.", "");
-                if (newResponse.ErrorMessage.Equals(SR.PasswordChangeEmptyPassword))
+                newResponse.ErrorMessage = ex.Message;
+                int errorCode = 0;
+
+                if ((ex.InnerException as SqlException) != null && (ex.InnerException as SqlException)?.Errors.Count != 0)
+                {
+                    SqlError endError = (ex.InnerException as SqlException).Errors[0];
+                    newResponse.ErrorMessage = endError.Message;
+                    errorCode = endError.Number;
+                }
+
+                if (errorCode == 0 && newResponse.ErrorMessage.Equals(SR.PasswordChangeEmptyPassword))
                 {
                     newResponse.ErrorMessage += Environment.NewLine + Environment.NewLine + SR.PasswordChangeEmptyPasswordRetry;
                 }
-                else if (newResponse.ErrorMessage.Contains(SR.PasswordChangeDNMReqs))
+                else if (errorCode == DoesNotMeetPWReqs)
                 {
                     newResponse.ErrorMessage += Environment.NewLine + Environment.NewLine + SR.PasswordChangeDNMReqsRetry;
                 }
-                else if (newResponse.ErrorMessage.Contains(SR.PasswordChangePWCannotBeUsed))
+                else if (errorCode == PWCannotBeUsed)
                 {
                     newResponse.ErrorMessage += Environment.NewLine + Environment.NewLine + SR.PasswordChangePWCannotBeUsedRetry;
                 }
diff --git a/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.cs b/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.cs
index 070e8359..449a3228 100644
--- a/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.cs
+++ b/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.cs
@@ -77,14 +77,6 @@ namespace Microsoft.SqlTools.ServiceLayer
             }
         }
 
-        public static string PasswordChangeDNMReqs
-        {
-            get
-            {
-                return Keys.GetString(Keys.PasswordChangeDNMReqs);
-            }
-        }
-
         public static string PasswordChangeDNMReqsRetry
         {
             get
@@ -93,14 +85,6 @@ namespace Microsoft.SqlTools.ServiceLayer
             }
         }
 
-        public static string PasswordChangePWCannotBeUsed
-        {
-            get
-            {
-                return Keys.GetString(Keys.PasswordChangePWCannotBeUsed);
-            }
-        }
-
         public static string PasswordChangePWCannotBeUsedRetry
         {
             get
@@ -10136,15 +10120,9 @@ namespace Microsoft.SqlTools.ServiceLayer
             public const string PasswordChangeEmptyPasswordRetry = "PasswordChangeEmptyPasswordRetry";
 
 
-            public const string PasswordChangeDNMReqs = "PasswordChangeDNMReqs";
-
-
             public const string PasswordChangeDNMReqsRetry = "PasswordChangeDNMReqsRetry";
 
 
-            public const string PasswordChangePWCannotBeUsed = "PasswordChangePWCannotBeUsed";
-
-
             public const string PasswordChangePWCannotBeUsedRetry = "PasswordChangePWCannotBeUsedRetry";
 
 
diff --git a/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.resx b/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.resx
index a5d8d954..71f8df03 100644
--- a/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.resx
+++ b/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.resx
@@ -176,18 +176,10 @@
     <value>Press OK to input a new password that is not empty.</value>
     <comment></comment>
   </data>
-  <data name="PasswordChangeDNMReqs" xml:space="preserve">
-    <value>password does not meet operating system policy requirements</value>
-    <comment></comment>
-  </data>
   <data name="PasswordChangeDNMReqsRetry" xml:space="preserve">
     <value>Press OK to input a new password that meets operating system policy requirements.</value>
     <comment></comment>
   </data>
-  <data name="PasswordChangePWCannotBeUsed" xml:space="preserve">
-    <value>password cannot be used at this time</value>
-    <comment></comment>
-  </data>
   <data name="PasswordChangePWCannotBeUsedRetry" xml:space="preserve">
     <value>Press OK to input a different password.</value>
     <comment></comment>
diff --git a/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.strings b/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.strings
index 07abb28e..930bb977 100644
--- a/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.strings
+++ b/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.strings
@@ -51,12 +51,8 @@ PasswordChangeEmptyPassword = New password cannot be empty
 
 PasswordChangeEmptyPasswordRetry = Press OK to input a new password that is not empty.
 
-PasswordChangeDNMReqs = password does not meet operating system policy requirements
-
 PasswordChangeDNMReqsRetry = Press OK to input a new password that meets operating system policy requirements.
 
-PasswordChangePWCannotBeUsed = password cannot be used at this time
-
 PasswordChangePWCannotBeUsedRetry = Press OK to input a different password.
 
 ### Connection Params Validation Errors
diff --git a/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.xlf b/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.xlf
index ba07576f..f1427633 100644
--- a/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.xlf
+++ b/src/Microsoft.SqlTools.ServiceLayer/Localization/sr.xlf
@@ -6515,21 +6515,11 @@ The Query Processor estimates that implementing the following index could improv
         <target state="new">Press OK to input a new password that is not empty.</target>
         <note></note>
       </trans-unit>
-      <trans-unit id="PasswordChangeDNMReqs">
-        <source>password does not meet operating system policy requirements</source>
-        <target state="new">password does not meet operating system policy requirements</target>
-        <note></note>
-      </trans-unit>
       <trans-unit id="PasswordChangeDNMReqsRetry">
         <source>Press OK to input a new password that meets operating system policy requirements.</source>
         <target state="new">Press OK to input a new password that meets operating system policy requirements.</target>
         <note></note>
       </trans-unit>
-      <trans-unit id="PasswordChangePWCannotBeUsed">
-        <source>password cannot be used at this time</source>
-        <target state="new">password cannot be used at this time</target>
-        <note></note>
-      </trans-unit>
       <trans-unit id="PasswordChangePWCannotBeUsedRetry">
         <source>Press OK to input a different password.</source>
         <target state="new">Press OK to input a different password.</target>