diff --git a/CHANGELOG.md b/CHANGELOG.md
index 586fb27..378313c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,10 @@
 # CHANGELOG
 
+## v2.27.0 (2024-11-22)
+
+* Resolved problem with EdgeWorkers CLI hitting cert issues in akamai/shell Docker image
+* Upgraded akamai terraform provider to v6.6.0
+
 ## v2.26.0 (2024-10-14)
 
 * DXE-3346 Upgrade alpine to 3.19 for `base`.
diff --git a/dockerfiles/httpie.Dockerfile b/dockerfiles/httpie.Dockerfile
index 30cfdc2..2c382fc 100644
--- a/dockerfiles/httpie.Dockerfile
+++ b/dockerfiles/httpie.Dockerfile
@@ -32,7 +32,7 @@ RUN apk add --no-cache python3 py3-pip py3-setuptools \
   # Activate the virtual environment
   && . /venv/bin/activate \
   && pip install --upgrade pip setuptools \
-  && pip install httpie httpie-edgegrid \
+  && pip install  pip-system-certs httpie httpie-edgegrid \
   # Drop dev dependencies
   && apk del dev \
   # Drop created wheels
diff --git a/files/terraform.tf b/files/terraform.tf
index 53c3d4e..13a296f 100644
--- a/files/terraform.tf
+++ b/files/terraform.tf
@@ -2,7 +2,7 @@ terraform {
   required_providers {
     akamai = {
       source = "akamai/akamai"
-      version = "6.5.0"
+      version = "6.6.0"
     }
 
     null = {