diff --git a/.changeset/cold-shirts-wonder.md b/.changeset/cold-shirts-wonder.md
new file mode 100644
index 0000000000..211cb6cd51
--- /dev/null
+++ b/.changeset/cold-shirts-wonder.md
@@ -0,0 +1,5 @@
+---
+"@medusajs/cli": patch
+---
+
+fix: log cause property from the error
diff --git a/packages/cli/medusa-cli/src/reporter/__tests__/__snapshots__/index.js.snap b/packages/cli/medusa-cli/src/reporter/__tests__/__snapshots__/index.js.snap
index ca294c5800..8aa31875c0 100644
--- a/packages/cli/medusa-cli/src/reporter/__tests__/__snapshots__/index.js.snap
+++ b/packages/cli/medusa-cli/src/reporter/__tests__/__snapshots__/index.js.snap
@@ -9,16 +9,10 @@ exports[`Reporter handles "Error" signature correctly 1`] = `
 `;
 
 exports[`Reporter handles "String" signature correctly 1`] = `
-{
-  "level": "error",
-  "message": "Test log",
-}
-`;
-
-exports[`Reporter handles "String, Error" signature correctly 1`] = `
-{
-  "level": "error",
-  "message": "Test log",
-  "stack": Any<Array>,
-}
+[
+  {
+    "level": "error",
+    "message": "Test log",
+  },
+]
 `;
diff --git a/packages/cli/medusa-cli/src/reporter/__tests__/index.js b/packages/cli/medusa-cli/src/reporter/__tests__/index.js
index d342439f28..d9bdf96d2a 100644
--- a/packages/cli/medusa-cli/src/reporter/__tests__/index.js
+++ b/packages/cli/medusa-cli/src/reporter/__tests__/index.js
@@ -1,4 +1,6 @@
 import { Reporter } from "../"
+import winston from "winston"
+import Transport from "winston-transport"
 
 describe(`Reporter`, () => {
   const winstonMock = {
@@ -21,20 +23,19 @@ describe(`Reporter`, () => {
 
   it(`handles "String" signature correctly`, () => {
     reporter.error("Test log")
-
-    const generated = getErrorMessages(winstonMock.log)[0]
-
-    expect(generated).toMatchSnapshot()
+    expect(getErrorMessages(winstonMock.log)).toMatchSnapshot()
   })
 
   it(`handles "String, Error" signature correctly`, () => {
     reporter.error("Test log", new Error("String Error"))
 
     const generated = getErrorMessages(winstonMock.log)[0]
-
-    expect(generated).toMatchSnapshot({
-      stack: expect.any(Array),
-    })
+    expect(generated).toMatchInlineSnapshot(`
+      {
+        "level": "error",
+        "message": "Test log",
+      }
+    `)
   })
 
   it(`handles "Error" signature correctly`, () => {
@@ -46,4 +47,73 @@ describe(`Reporter`, () => {
       stack: expect.any(Array),
     })
   })
+
+  it(`should display error cause when using json formatter`, () => {
+    class MemoryTransport extends Transport {
+      logs = []
+      log(info, callback) {
+        this.logs.push(info)
+        callback()
+      }
+    }
+    const transport = new MemoryTransport()
+
+    const jsonReporter = new Reporter({
+      logger: winston.createLogger({
+        level: "info",
+        levels: winston.config.npm.levels,
+        format: winston.format.combine(
+          winston.format.timestamp({
+            format: "YYYY-MM-DD HH:mm:ss",
+          }),
+          winston.format.errors({ stack: true }),
+          winston.format.splat(),
+          winston.format.json()
+        ),
+        transports: [transport],
+      }),
+    })
+    jsonReporter.error(new Error("Error", { cause: new Error("Nested error") }))
+
+    expect(transport.logs).toHaveLength(1)
+    expect(transport.logs[0]).toHaveProperty("cause")
+    expect(transport.logs[0].cause).toMatch("Nested error")
+  })
+
+  it(`should display custom message and error cause when using json formatter`, () => {
+    class MemoryTransport extends Transport {
+      logs = []
+      log(info, callback) {
+        this.logs.push(info)
+        callback()
+      }
+    }
+    const transport = new MemoryTransport()
+
+    const jsonReporter = new Reporter({
+      logger: winston.createLogger({
+        level: "info",
+        levels: winston.config.npm.levels,
+        format: winston.format.combine(
+          winston.format.timestamp({
+            format: "YYYY-MM-DD HH:mm:ss",
+          }),
+          winston.format.errors({ stack: true }),
+          winston.format.splat(),
+          winston.format.json()
+        ),
+        transports: [transport],
+      }),
+    })
+    jsonReporter.error(
+      "Something went wrong",
+      new Error("Error", { cause: new Error("Nested error") })
+    )
+
+    expect(transport.logs).toHaveLength(2)
+    expect(transport.logs[0].message).toEqual("Something went wrong")
+    expect(transport.logs[1].message).toEqual("Error")
+    expect(transport.logs[1]).toHaveProperty("cause")
+    expect(transport.logs[1].cause).toMatch("Nested error")
+  })
 })
diff --git a/packages/cli/medusa-cli/src/reporter/index.ts b/packages/cli/medusa-cli/src/reporter/index.ts
index 661fffb8ba..a582545e3c 100644
--- a/packages/cli/medusa-cli/src/reporter/index.ts
+++ b/packages/cli/medusa-cli/src/reporter/index.ts
@@ -1,8 +1,9 @@
-import { track } from "@medusajs/telemetry"
 import ora from "ora"
-import stackTrace from "stack-trace"
 import { ulid } from "ulid"
 import winston from "winston"
+import { inspect } from "util"
+import stackTrace from "stack-trace"
+import { track } from "@medusajs/telemetry"
 import { panicHandler } from "./panic-handler"
 
 const LOG_LEVEL = process.env.LOG_LEVEL || "http"
@@ -174,11 +175,17 @@ export class Reporter {
    * Level 0
    */
   error(messageOrError: string | Error, error?: Error) {
-    let message = messageOrError as string
+    let message: string
+    let errorAsObject: Error | undefined
 
-    if (typeof messageOrError === "object") {
+    if (messageOrError && typeof messageOrError === "object") {
+      errorAsObject = messageOrError
       message = messageOrError.message
-      error = messageOrError
+    } else if (error) {
+      message = messageOrError
+      errorAsObject = error
+    } else {
+      message = messageOrError
     }
 
     const toLog = {
@@ -186,15 +193,38 @@ export class Reporter {
       message,
     }
 
-    if (error) {
-      toLog["stack"] = stackTrace.parse(error)
+    if (errorAsObject) {
+      toLog["message"] = errorAsObject.message
+      toLog["stack"] = stackTrace.parse(errorAsObject)
+      /**
+       * Winston only logs the error properties when they are
+       * string values. Hence we will have to self convert
+       * the error cause to a string
+       */
+      if ("cause" in errorAsObject) {
+        toLog["cause"] = inspect(errorAsObject.cause)
+      }
     }
 
+    /**
+     * If "errorAsObject" has a message property, then we will
+     * print the standalone message as one log item and then
+     * the actual error object as another log item.
+     *
+     * Otherwise, we always loose the message property from the
+     * actual error object
+     */
+    if (errorAsObject?.message && errorAsObject?.message !== message) {
+      this.loggerInstance_.log({ level: "error", message })
+    }
     this.loggerInstance_.log(toLog)
 
-    // Give stack traces and details in dev
-    if (error && IS_DEV) {
-      console.log(error)
+    /**
+     * In dev we print the error using `console.error`, because Winston
+     * CLI formatter does not print the error stack in that case
+     */
+    if (errorAsObject && IS_DEV) {
+      console.error(errorAsObject)
     }
   }