diff --git a/tool/src/main/java/org/wildfly/security/tool/Command.java b/tool/src/main/java/org/wildfly/security/tool/Command.java
index 0659183dcd6..0bcc04e110b 100644
--- a/tool/src/main/java/org/wildfly/security/tool/Command.java
+++ b/tool/src/main/java/org/wildfly/security/tool/Command.java
@@ -44,10 +44,10 @@
 
 import javax.crypto.SecretKey;
 
-import org.wildfly.security.credential.Credential;
 import org.wildfly.security.credential.SecretKeyCredential;
 import org.wildfly.security.credential.store.CredentialStore;
 import org.wildfly.security.credential.store.CredentialStoreException;
+import org.wildfly.security.credential.store.UnsupportedCredentialTypeException;
 import org.wildfly.security.credential.store.impl.PropertiesCredentialStore;
 import org.wildfly.security.encryption.SecretKeyUtil;
 import org.wildfly.security.password.WildFlyElytronPasswordProvider;
@@ -204,7 +204,7 @@ public void printDuplicatesWarning(CommandLine cmdLine) {
      *                          <code>
      *                              List<String> allowedDuplicates = new ArrayList<String>()
      *                                  {{ add(PASSWORD_CREDENTIAL_VALUE_PARAM);
- *                                  }};
+     *                              }};
      *                          </code>
      */
     public void printDuplicatesWarning(CommandLine cmdLine, List<String> duplicatesAllowed) {
@@ -324,7 +324,7 @@ protected Supplier<Provider[]> getProvidersSupplier(final String providersList)
      * @throws Exception when an existing credential store does not contain the secret key
      */
     SecretKey getSecretKey(Boolean createCredentialStore, String credentialStoreLocation, String alias, Boolean populate,
-                           String inputRealmLocation) throws Exception {
+                           int descriptorBlockCount) throws Exception {
         CredentialStore credentialStore;
         String csType = PropertiesCredentialStore.NAME;
         try {
@@ -337,29 +337,42 @@ SecretKey getSecretKey(Boolean createCredentialStore, String credentialStoreLoca
         implProps.put("create", String.valueOf(createCredentialStore));
         implProps.put("location", credentialStoreLocation);
         implProps.put("modifiable", Boolean.TRUE.toString());
-        credentialStore.initialize(implProps);
+
         try {
-            credentialStore.retrieve(alias, SecretKeyCredential.class).getSecretKey();
+            credentialStore.initialize(implProps);
+        } catch (CredentialStoreException e) {
+            warningHandler(ElytronToolMessages.msg.skippingDescriptorBlockCredentialStoreNotLoaded(descriptorBlockCount));
+        }
+
+        SecretKeyCredential secretKeyCredential;
+        try {
+            secretKeyCredential = credentialStore.retrieve(alias, SecretKeyCredential.class);
+        } catch (UnsupportedCredentialTypeException e) {
+            warningHandler(ElytronToolMessages.msg.skippingDescriptorBlockSecretKeyUnsupported(credentialStoreLocation, descriptorBlockCount));
+            return null;
+        }
+
+        // Acquire SecretKey, and populate credential store if set
+        SecretKey key;
+        if (secretKeyCredential != null) {
             System.out.println(ElytronToolMessages.msg.existingCredentialStore());
-        } catch (Exception e) {
-            if (!createCredentialStore) {
-                warningHandler(ElytronToolMessages.msg.skippingBlockMissingCredentialStore());
-                return null;
-            }
-            if (populate) {
-                SecretKey key = SecretKeyUtil.generateSecretKey(256);
-                Credential keyCredential = new SecretKeyCredential(key);
-                credentialStore.store(alias, keyCredential);
+            key = secretKeyCredential.getSecretKey();
+        } else if (populate) {
+            try {
+                SecretKey newKey = SecretKeyUtil.generateSecretKey(256);
+                SecretKeyCredential newKeyCredential = new SecretKeyCredential(newKey);
+                credentialStore.store(alias, newKeyCredential);
                 credentialStore.flush();
-            } else {
-                errorHandler(ElytronToolMessages.msg.cmdFileSystemPopulateUnspecified());
+
+                key = newKey;
+            } catch (GeneralSecurityException e) {
+                warningHandler(ElytronToolMessages.msg.skippingDescriptorBlockUnableToPopulateCredentialStore(
+                        credentialStoreLocation, descriptorBlockCount));
+                return null;
             }
-        }
-        SecretKey key;
-        try {
-            key = credentialStore.retrieve(alias, SecretKeyCredential.class).getSecretKey();
-        } catch (NullPointerException e) {
-            System.out.println(ElytronToolMessages.msg.cmdFileSystemEncryptionNoSecretKey(credentialStoreLocation, inputRealmLocation));
+
+        } else {
+            warningHandler(ElytronToolMessages.msg.cmdFileSystemEncryptionNoSecretKey(credentialStoreLocation, descriptorBlockCount));
             return null;
         }
 
diff --git a/tool/src/main/java/org/wildfly/security/tool/ElytronToolMessages.java b/tool/src/main/java/org/wildfly/security/tool/ElytronToolMessages.java
index cc3d1531150..d47bf892e30 100644
--- a/tool/src/main/java/org/wildfly/security/tool/ElytronToolMessages.java
+++ b/tool/src/main/java/org/wildfly/security/tool/ElytronToolMessages.java
@@ -485,11 +485,8 @@ public interface ElytronToolMessages extends BasicLogger {
     @Message(id = NONE, value = "'FileSystemRealmEncrypt' command is used to convert un-encrypted FileSystemSecurityRealm(s) to encrypted FileSystemSecurityRealm(s) with a SecretKey.")
     String cmdFileSystemEncryptHelpHeader();
 
-    @Message(id = NONE, value = "The populate parameter was set to false and the Secret Key did not exist in the Credential Store.")
-    MissingOptionException cmdFileSystemPopulateUnspecified();
-
-    @Message(id = NONE, value = "Unable to locate Secret Key with Credential Store located at %s. Skipping realm located at %s.")
-    String cmdFileSystemEncryptionNoSecretKey(String credentialStore, String realmLocation);
+    @Message(id = NONE, value = "Secret Key was not found in the Credential Store at %s, and populate option was not set. Skipping descriptor file block number %d.")
+    String cmdFileSystemEncryptionNoSecretKey(String credentialStorePath, Integer blockNumber);
 
     @Message(id = NONE, value = "The character set used to convert the password string to a byte array. Defaults to UTF-8.")
     String cmdFileSystemRealmIntegrityHashCharsetDesc();
@@ -600,8 +597,14 @@ public interface ElytronToolMessages extends BasicLogger {
     @Message(id = NONE, value = "Found credential store and alias, using pre-existing key")
     String existingCredentialStore();
 
-    @Message(id = NONE, value = "Could not find credential store and secret key alias, skipping block")
-    String skippingBlockMissingCredentialStore();
+    @Message(id = NONE, value = "Skipping descriptor file block number %d due to failure to load Credential Store.")
+    String skippingDescriptorBlockCredentialStoreNotLoaded(Integer blockNumber);
+
+    @Message(id = NONE, value = "Credential Store at %s does not support SecretKey. Skipping descriptor file block number %d.")
+    String skippingDescriptorBlockSecretKeyUnsupported(String credentialStorePath, Integer blockNumber);
+
+    @Message(id = NONE, value = "Exception was thrown while populating Credential Store at %s. Skipping descriptor file block number %d.")
+    String skippingDescriptorBlockUnableToPopulateCredentialStore(String credentialStorePath, Integer blockNumber);
 
     @Message(id = NONE, value = "No Credential Store location or Secret Key Alias specified.")
     MissingOptionException missingCredentialStoreSecretKey();
diff --git a/tool/src/main/java/org/wildfly/security/tool/FileSystemEncryptRealmCommand.java b/tool/src/main/java/org/wildfly/security/tool/FileSystemEncryptRealmCommand.java
index 34f4d090dd8..4b0796c6189 100644
--- a/tool/src/main/java/org/wildfly/security/tool/FileSystemEncryptRealmCommand.java
+++ b/tool/src/main/java/org/wildfly/security/tool/FileSystemEncryptRealmCommand.java
@@ -689,14 +689,16 @@ private void findMissingRequiredValuesAndSetValues(int count, Descriptor descrip
      */
 
     private void createFileSystemRealm() throws Exception {
+        int blockCount = 0;
         for (Descriptor descriptor : descriptors) {
+            blockCount++;
             System.out.println(ElytronToolMessages.msg.fileSystemRealmEncryptCreatingRealm(descriptor.getInputRealmLocation()));
 
             if (checkDescriptorFields(descriptor)) continue;
 
             // Load secret key
             SecretKey key = getSecretKey(descriptor.getCreateCredentialStore(), descriptor.getCredentialStore(),
-                    descriptor.getSecretKeyAlias(), descriptor.getPopulate(), descriptor.getInputRealmLocation());
+                    descriptor.getSecretKeyAlias(), descriptor.getPopulate(), blockCount);
             if (key == null) continue;
 
             FileSystemSecurityRealm oldFileSystemRealm = FileSystemSecurityRealm.builder()