diff --git a/CHANGELOG.md b/CHANGELOG.md
index 269475c..f32b1a3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@ Note: Breaking changes between versions are indicated by "💥".
 
 ## Unreleased
 
+- [Bugfix] During upgrade, make sure that environment is up-to-date prior to prompting to rebuild the custom images.
 - [Bugfix] Fix ownership of mysql data, in particular when upgrading a Kubernetes cluster to Maple.
 - [Bugfix] Ensure that ``tutor k8s upgrade`` is run during ``tutor k8s quickstart``, when necessary.
 - [Bugfix] By default, upgrade from Lilac and not Koa during ``tutor k8s upgrade``.
diff --git a/tutor/commands/k8s.py b/tutor/commands/k8s.py
index 0c0283d..d01b169 100644
--- a/tutor/commands/k8s.py
+++ b/tutor/commands/k8s.py
@@ -162,6 +162,7 @@ def quickstart(context: click.Context, non_interactive: bool) -> None:
         context.invoke(
             upgrade,
             from_version=tutor_env.current_release(context.obj.root),
+            non_interactive=non_interactive,
         )
 
     click.echo(fmt.title("Interactive platform configuration"))
@@ -448,8 +449,9 @@ def wait(context: Context, name: str) -> None:
     default="lilac",
     type=click.Choice(["ironwood", "juniper", "koa", "lilac"]),
 )
+@click.option("-I", "--non-interactive", is_flag=True, help="Run non-interactively")
 @click.pass_obj
-def upgrade(context: Context, from_version: str) -> None:
+def upgrade(context: Context, from_version: str, non_interactive: bool) -> None:
     config = tutor_config.load(context.root)
 
     running_version = from_version
@@ -469,6 +471,23 @@ def upgrade(context: Context, from_version: str) -> None:
         upgrade_from_lilac(config)
         running_version = "maple"
 
+    # Update env such that the build environment is up-to-date
+    tutor_env.save(context.root, config)
+    if not non_interactive:
+        question = f"""
+Your platform was successfuly upgraded from {from_version} to {running_version}.
+Depending on your setup, you might have to rebuild some of your Docker images
+and push them to your private registry (if any). You can do this now by running
+the following command in a different shell:
+
+    tutor images build openedx # add your custom images here
+    tutor images push openedx
+
+Press enter when you are ready to continue"""
+        click.confirm(
+            fmt.question(question), default=True, abort=True, prompt_suffix=" "
+        )
+
 
 def upgrade_from_ironwood(config: Config) -> None:
     if not config["RUN_MONGODB"]:
diff --git a/tutor/commands/local.py b/tutor/commands/local.py
index 49da6d9..0b30634 100644
--- a/tutor/commands/local.py
+++ b/tutor/commands/local.py
@@ -105,7 +105,7 @@ Your Open edX platform is ready and can be accessed at the following urls:
 @click.option("-I", "--non-interactive", is_flag=True, help="Run non-interactively")
 @click.pass_context
 def upgrade(context: click.Context, from_version: str, non_interactive: bool) -> None:
-    config = tutor_config.load_full(context.obj.root)
+    config = tutor_config.load(context.obj.root)
 
     if not non_interactive:
         question = """You are about to upgrade your Open edX platform. It is strongly recommended to make a backup before upgrading. To do so, run:
@@ -137,9 +137,13 @@ Are you sure you want to continue?"""
         # Nothing to do here
         running_version = "maple"
 
+    # Update env such that the build environment is up-to-date
+    tutor_env.save(context.obj.root, config)
     if not non_interactive:
         question = f"""
-Your platform was successfuly upgraded from {from_version} to {running_version}. Depending on your setup, you might have to rebuild some of your Docker images. You can do this now by running the following command in a different shell:
+Your platform was successfuly upgraded from {from_version} to {running_version}.
+Depending on your setup, you might have to rebuild some of your Docker images.
+You can do this now by running the following command in a different shell:
 
     tutor images build openedx # add your custom images here