diff --git a/roles/custom/matrix-static-files/defaults/main.yml b/roles/custom/matrix-static-files/defaults/main.yml
index b52e9540c..89fb02a33 100644
--- a/roles/custom/matrix-static-files/defaults/main.yml
+++ b/roles/custom/matrix-static-files/defaults/main.yml
@@ -57,6 +57,11 @@ matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_priority
 matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_entrypoints: "{{ matrix_static_files_container_labels_traefik_entrypoints }}"
 matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_tls: "{{ matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_entrypoints != 'web' }}"
 matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_tls_certResolver: "{{ matrix_static_files_container_labels_traefik_tls_certResolver }}"  # noqa var-naming
+# Controls whether the compress middleware (https://doc.traefik.io/traefik/middlewares/http/compress/) will be enabled for this router.
+# The web-server only compresses known file types and our /.well-known/matrix/* files have no file extension.
+# As such, they are not being compressed there and we compress them at the Traefik level.
+matrix_static_files_container_labels_well_known_matrix_endpoint_middleware_compress_enabled: true
+matrix_static_files_container_labels_well_known_matrix_endpoint_middleware_compress_minResponseBodyBytes: 100 # noqa var-naming
 
 # Controls whether labels will be added that serve the base domain.
 #
@@ -77,7 +82,6 @@ matrix_static_files_container_labels_base_domain_traefik_entrypoints: "{{ matrix
 matrix_static_files_container_labels_base_domain_traefik_tls: "{{ matrix_static_files_container_labels_base_domain_traefik_entrypoints != 'web' }}"
 matrix_static_files_container_labels_base_domain_traefik_tls_certResolver: "{{ matrix_static_files_container_labels_traefik_tls_certResolver }}"  # noqa var-naming
 
-
 # matrix_static_files_container_labels_additional_labels contains a multiline string with additional labels to add to the container label file.
 # See `../templates/labels.j2` for details.
 #
diff --git a/roles/custom/matrix-static-files/templates/labels.j2 b/roles/custom/matrix-static-files/templates/labels.j2
index 6f49b4018..6b9c17b72 100644
--- a/roles/custom/matrix-static-files/templates/labels.j2
+++ b/roles/custom/matrix-static-files/templates/labels.j2
@@ -13,11 +13,19 @@ traefik.http.services.{{ matrix_static_files_ident }}.loadbalancer.server.port={
 #}
 {% if matrix_static_files_container_labels_well_known_matrix_endpoint_enabled %}
 
+{% set well_known_matrix_endpoint_middlewares = [] %}
+
+{% if matrix_static_files_container_labels_well_known_matrix_endpoint_middleware_compress_enabled %}
 traefik.http.middlewares.{{ matrix_static_files_ident }}-well-known-endpoint-compress.compress=true
-traefik.http.middlewares.{{ matrix_static_files_ident }}-well-known-endpoint-compress.compress.minResponseBodyBytes=100
+traefik.http.middlewares.{{ matrix_static_files_ident }}-well-known-endpoint-compress.compress.minResponseBodyBytes={{ matrix_static_files_container_labels_well_known_matrix_endpoint_middleware_compress_minResponseBodyBytes }}
+{% set well_known_matrix_endpoint_middlewares = well_known_matrix_endpoint_middlewares + [matrix_static_files_ident + '-well-known-endpoint-compress'] %}
+{% endif %}
 
 traefik.http.routers.{{ matrix_static_files_ident }}-well-known-endpoint.rule={{ matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_rule }}
-traefik.http.routers.{{ matrix_static_files_ident }}-well-known-endpoint.middlewares={{ matrix_static_files_ident }}-well-known-endpoint-compress
+
+{% if well_known_matrix_endpoint_middlewares | length > 0 %}
+traefik.http.routers.{{ matrix_static_files_ident }}-well-known-endpoint.middlewares={{ well_known_matrix_endpoint_middlewares | join(',') }}
+{% endif %}
 
 {% if matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_priority | int > 0 %}
 traefik.http.routers.{{ matrix_static_files_ident }}-well-known-endpoint.priority={{ matrix_static_files_container_labels_well_known_matrix_endpoint_traefik_priority }}