diff --git a/src/main/java/io/jenkins/plugins/jfrog/CliEnvConfigurator.java b/src/main/java/io/jenkins/plugins/jfrog/CliEnvConfigurator.java
index 6cf4cdc9..afde3ae8 100644
--- a/src/main/java/io/jenkins/plugins/jfrog/CliEnvConfigurator.java
+++ b/src/main/java/io/jenkins/plugins/jfrog/CliEnvConfigurator.java
@@ -49,10 +49,11 @@ static void configureCliEnv(EnvVars env, FilePath jfrogHomeTempDir, JFrogCliConf
             setupProxy(env);
         }
         if (encryptionKey.shouldEncrypt()) {
-            // Write the encryption key file on the agent (not controller) using FilePath.
-            // This ensures the file exists where the JFrog CLI runs (Docker/remote agent).
+            // Write the encryption key file on the current agent using FilePath.
+            // Always overwrite (not putIfAbsent) because in multi-agent pipelines the env
+            // var may still hold the previous agent's path, which doesn't exist on this agent.
             String keyFilePath = encryptionKey.writeKeyFile(jfrogHomeTempDir);
-            env.putIfAbsent(JFROG_CLI_ENCRYPTION_KEY, keyFilePath);
+            env.put(JFROG_CLI_ENCRYPTION_KEY, keyFilePath);
         }
     }
 
diff --git a/src/main/java/io/jenkins/plugins/jfrog/actions/JFrogCliConfigEncryption.java b/src/main/java/io/jenkins/plugins/jfrog/actions/JFrogCliConfigEncryption.java
index 1d5f3bde..90c972bd 100644
--- a/src/main/java/io/jenkins/plugins/jfrog/actions/JFrogCliConfigEncryption.java
+++ b/src/main/java/io/jenkins/plugins/jfrog/actions/JFrogCliConfigEncryption.java
@@ -36,6 +36,10 @@ public JFrogCliConfigEncryption(EnvVars env) {
     /**
      * Writes the encryption key to a file in the specified directory on the agent.
      * Uses FilePath to ensure the file is written on the remote agent, not the controller.
+     * <p>
+     * The key file is always written fresh to the given jfrogHomeTempDir. In multi-agent
+     * pipelines each agent has its own filesystem, so the file must be written locally on
+     * every agent where the JFrog CLI runs. The key content stays the same across agents.
      *
      * @param jfrogHomeTempDir - The JFrog CLI home temp directory (FilePath on the agent)
      * @return The path to the key file (as seen by the agent)
@@ -46,17 +50,15 @@ public String writeKeyFile(FilePath jfrogHomeTempDir) throws IOException, Interr
         if (this.key == null || this.key.isEmpty()) {
             return null;
         }
-        // If key file was already written, return the existing path
-        if (this.keyFilePath != null) {
-            return this.keyFilePath;
-        }
-        // Use FilePath operations to write on the agent (not controller)
+        // Always write the key file on the current agent's filesystem.
+        // Do NOT cache/reuse keyFilePath: in multi-agent pipelines each agent has its own
+        // filesystem, so returning a previously cached path would point to a different
+        // agent's file which does not exist on the current agent.
         FilePath encryptionDir = jfrogHomeTempDir.child("encryption");
         encryptionDir.mkdirs();
         String fileName = UUID.randomUUID().toString() + ".key";
         FilePath keyFile = encryptionDir.child(fileName);
         keyFile.write(this.key, StandardCharsets.UTF_8.name());
-        // getRemote() returns the path as seen by the agent
         this.keyFilePath = keyFile.getRemote();
         return this.keyFilePath;
     }