diff --git a/Dockerfile b/Dockerfile
index 2af6f55..dec431a 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,7 +1,7 @@
 # Setup build arguments
 ARG AWS_CLI_VERSION
 ARG TERRAFORM_VERSION
-ARG DEBIAN_VERSION=bookworm-20231120-slim
+ARG DEBIAN_VERSION=bookworm-20260316-slim
 ARG DEBIAN_FRONTEND=noninteractive
 
 # Download Terraform binary
@@ -9,10 +9,9 @@ FROM debian:${DEBIAN_VERSION} as terraform
 ARG TARGETARCH
 ARG TERRAFORM_VERSION
 RUN apt-get update
-# RUN apt-get install --no-install-recommends -y libcurl4=7.74.0-1.3+deb11u7
-RUN apt-get install --no-install-recommends -y ca-certificates=20230311
-RUN apt-get install --no-install-recommends -y curl=7.88.1-10+deb12u4
-RUN apt-get install --no-install-recommends -y gnupg=2.2.40-1.1
+RUN apt-get install --no-install-recommends -y ca-certificates=20230311+deb12u1
+RUN apt-get install --no-install-recommends -y curl=7.88.1-10+deb12u14
+RUN apt-get install --no-install-recommends -y gnupg=2.2.40-1.1+deb12u2
 RUN apt-get install --no-install-recommends -y unzip=6.0-28
 WORKDIR /workspace
 RUN curl --silent --show-error --fail --remote-name https://releases.hashicorp.com/terraform/${TERRAFORM_VERSION}/terraform_${TERRAFORM_VERSION}_linux_${TARGETARCH}.zip
@@ -27,12 +26,12 @@ RUN unzip -j terraform_${TERRAFORM_VERSION}_linux_${TARGETARCH}.zip
 FROM debian:${DEBIAN_VERSION} as aws-cli
 ARG AWS_CLI_VERSION
 RUN apt-get update
-RUN apt-get install -y --no-install-recommends ca-certificates=20230311
-RUN apt-get install -y --no-install-recommends curl=7.88.1-10+deb12u4
-RUN apt-get install -y --no-install-recommends gnupg=2.2.40-1.1
+RUN apt-get install --no-install-recommends -y ca-certificates=20230311+deb12u1
+RUN apt-get install --no-install-recommends -y curl=7.88.1-10+deb12u14
+RUN apt-get install --no-install-recommends -y gnupg=2.2.40-1.1+deb12u2
 RUN apt-get install -y --no-install-recommends unzip=6.0-28
-RUN apt-get install -y --no-install-recommends git=1:2.39.2-1.1
-RUN apt-get install -y --no-install-recommends jq=1.6-2.1
+RUN apt-get install -y --no-install-recommends git=1:2.39.5-0+deb12u3
+RUN apt-get install -y --no-install-recommends jq=1.6-2.1+deb12u1
 WORKDIR /workspace
 RUN curl --show-error --fail --output "awscliv2.zip" --remote-name "https://awscli.amazonaws.com/awscli-exe-linux-x86_64-${AWS_CLI_VERSION}.zip"
 COPY security/awscliv2.asc ./
@@ -47,10 +46,10 @@ FROM debian:${DEBIAN_VERSION} as build
 LABEL maintainer="bgauduch@github"
 RUN apt-get update \
   && apt-get install -y --no-install-recommends \
-    ca-certificates=20230311\
-    git=1:2.39.2-1.1 \
-    jq=1.6-2.1 \
-    openssh-client=1:9.2p1-2+deb12u1 \
+    ca-certificates=20230311+deb12u1\
+    git=1:2.39.5-0+deb12u3 \
+    jq=1.6-2.1+deb12u1 \
+    openssh-client=1:9.2p1-2+deb12u7 \
   && apt-get clean \
   && rm -rf /var/lib/apt/lists/*
 WORKDIR /workspace
diff --git a/security/awscli-exe-linux-x86_64-2.14.5.zip.sig b/security/awscli-exe-linux-x86_64-2.14.5.zip.sig
deleted file mode 100644
index b39fefa..0000000
Binary files a/security/awscli-exe-linux-x86_64-2.14.5.zip.sig and /dev/null differ
diff --git a/security/awscli-exe-linux-x86_64-2.17.4.zip.sig b/security/awscli-exe-linux-x86_64-2.17.4.zip.sig
new file mode 100644
index 0000000..54abf77
Binary files /dev/null and b/security/awscli-exe-linux-x86_64-2.17.4.zip.sig differ
diff --git a/security/awscli-exe-linux-x86_64-2.34.17.zip.sig b/security/awscli-exe-linux-x86_64-2.34.17.zip.sig
new file mode 100644
index 0000000..d9576e0
Binary files /dev/null and b/security/awscli-exe-linux-x86_64-2.34.17.zip.sig differ
diff --git a/security/awscliv2.asc b/security/awscliv2.asc
index 5951848..805491c 100644
--- a/security/awscliv2.asc
+++ b/security/awscliv2.asc
@@ -11,19 +11,19 @@ lrFj6UwAsGukBTAOxC0l/dnSmZhJ7Z1KmEWilro/gOrjtOxqRQutlIqG22TaqoPG
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-=vYOk
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+j+c7Kg92pDx2uQ==
+=OBAt
 -----END PGP PUBLIC KEY BLOCK-----
diff --git a/security/terraform_1.10.3_SHA256SUMS b/security/terraform_1.10.3_SHA256SUMS
new file mode 100644
index 0000000..48ff97a
--- /dev/null
+++ b/security/terraform_1.10.3_SHA256SUMS
@@ -0,0 +1,14 @@
+a7ff68a57ead3ca7ac0a4d055b5f08a2ce0474e371d935e75398fe7f864ba65e  terraform_1.10.3_darwin_amd64.zip
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+1bcce40eadc8f386353cad5b41d10b3618f2a967f027c177f5aa95337e499b9f  terraform_1.10.3_freebsd_amd64.zip
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+f255e91b6d18ed7fdfffc32beff3877583ccce19d239685e9521e49c36b88f14  terraform_1.10.3_linux_386.zip
+ea3020db6b53c25a4a84e40cdc36c1a86df26967d718219ab4c71b44435da81e  terraform_1.10.3_linux_amd64.zip
+829bf0965dbae58e88fc885159889908583220b5fff4ca8ff34326534a824dbd  terraform_1.10.3_linux_arm.zip
+b92d8245c67d4f7193245bc9d534048a63520302b6edb3c7764277b00c96ed31  terraform_1.10.3_linux_arm64.zip
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+a3956ef0d347c82b481dbe8ec9ced97ba729df0a2e84eebce99d56de57d2e470  terraform_1.10.3_solaris_amd64.zip
+ca2e73f365b7cbefd8d45c80eae06f98b7fff2a3e1bb426e15f7ef9ed59d38de  terraform_1.10.3_windows_386.zip
+9d465d32a833843962fc6a93f74d170c93716e34c0b6480e21650ce84426ae86  terraform_1.10.3_windows_amd64.zip
diff --git a/security/terraform_1.10.3_SHA256SUMS.sig b/security/terraform_1.10.3_SHA256SUMS.sig
new file mode 100644
index 0000000..08882ab
Binary files /dev/null and b/security/terraform_1.10.3_SHA256SUMS.sig differ
diff --git a/security/terraform_1.10.5_SHA256SUMS b/security/terraform_1.10.5_SHA256SUMS
new file mode 100644
index 0000000..faf31f7
--- /dev/null
+++ b/security/terraform_1.10.5_SHA256SUMS
@@ -0,0 +1,14 @@
+4164db242076c7e99ac6aec67bc42b366925b97267e3883edaca4e4e408b082e  terraform_1.10.5_darwin_amd64.zip
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diff --git a/security/terraform_1.10.5_SHA256SUMS.sig b/security/terraform_1.10.5_SHA256SUMS.sig
new file mode 100644
index 0000000..f3a64aa
Binary files /dev/null and b/security/terraform_1.10.5_SHA256SUMS.sig differ
diff --git a/security/terraform_1.11.4_SHA256SUMS b/security/terraform_1.11.4_SHA256SUMS
new file mode 100644
index 0000000..f9acd36
--- /dev/null
+++ b/security/terraform_1.11.4_SHA256SUMS
@@ -0,0 +1,14 @@
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diff --git a/security/terraform_1.11.4_SHA256SUMS.sig b/security/terraform_1.11.4_SHA256SUMS.sig
new file mode 100644
index 0000000..d3bcfbb
Binary files /dev/null and b/security/terraform_1.11.4_SHA256SUMS.sig differ
diff --git a/security/terraform_1.12.2_SHA256SUMS b/security/terraform_1.12.2_SHA256SUMS
new file mode 100644
index 0000000..b299eed
--- /dev/null
+++ b/security/terraform_1.12.2_SHA256SUMS
@@ -0,0 +1,14 @@
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diff --git a/security/terraform_1.12.2_SHA256SUMS.sig b/security/terraform_1.12.2_SHA256SUMS.sig
new file mode 100644
index 0000000..714bdb2
Binary files /dev/null and b/security/terraform_1.12.2_SHA256SUMS.sig differ
diff --git a/security/terraform_1.14.8_SHA256SUMS b/security/terraform_1.14.8_SHA256SUMS
new file mode 100644
index 0000000..df08098
--- /dev/null
+++ b/security/terraform_1.14.8_SHA256SUMS
@@ -0,0 +1,14 @@
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diff --git a/security/terraform_1.14.8_SHA256SUMS.sig b/security/terraform_1.14.8_SHA256SUMS.sig
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index 0000000..8aae7ad
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diff --git a/security/terraform_1.6.5_SHA256SUMS b/security/terraform_1.6.5_SHA256SUMS
deleted file mode 100644
index 2e1a647..0000000
--- a/security/terraform_1.6.5_SHA256SUMS
+++ /dev/null
@@ -1,14 +0,0 @@
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diff --git a/security/terraform_1.6.5_SHA256SUMS.sig b/security/terraform_1.6.5_SHA256SUMS.sig
deleted file mode 100644
index ee810ed..0000000
Binary files a/security/terraform_1.6.5_SHA256SUMS.sig and /dev/null differ
diff --git a/security/terraform_1.6.6_SHA256SUMS b/security/terraform_1.6.6_SHA256SUMS
new file mode 100644
index 0000000..28aae5e
--- /dev/null
+++ b/security/terraform_1.6.6_SHA256SUMS
@@ -0,0 +1,14 @@
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diff --git a/security/terraform_1.6.6_SHA256SUMS.sig b/security/terraform_1.6.6_SHA256SUMS.sig
new file mode 100644
index 0000000..ccb6861
Binary files /dev/null and b/security/terraform_1.6.6_SHA256SUMS.sig differ
diff --git a/security/terraform_1.7.5_SHA256SUMS b/security/terraform_1.7.5_SHA256SUMS
new file mode 100644
index 0000000..d0e0d00
--- /dev/null
+++ b/security/terraform_1.7.5_SHA256SUMS
@@ -0,0 +1,14 @@
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diff --git a/security/terraform_1.7.5_SHA256SUMS.sig b/security/terraform_1.7.5_SHA256SUMS.sig
new file mode 100644
index 0000000..1b5ba45
Binary files /dev/null and b/security/terraform_1.7.5_SHA256SUMS.sig differ
diff --git a/security/terraform_1.8.5_SHA256SUMS b/security/terraform_1.8.5_SHA256SUMS
new file mode 100644
index 0000000..a4c096f
--- /dev/null
+++ b/security/terraform_1.8.5_SHA256SUMS
@@ -0,0 +1,14 @@
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diff --git a/security/terraform_1.8.5_SHA256SUMS.sig b/security/terraform_1.8.5_SHA256SUMS.sig
new file mode 100644
index 0000000..93d647e
Binary files /dev/null and b/security/terraform_1.8.5_SHA256SUMS.sig differ
diff --git a/security/terraform_1.9.8_SHA256SUMS b/security/terraform_1.9.8_SHA256SUMS
new file mode 100644
index 0000000..c901f5d
--- /dev/null
+++ b/security/terraform_1.9.8_SHA256SUMS
@@ -0,0 +1,14 @@
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diff --git a/security/terraform_1.9.8_SHA256SUMS.sig b/security/terraform_1.9.8_SHA256SUMS.sig
new file mode 100644
index 0000000..e591a43
Binary files /dev/null and b/security/terraform_1.9.8_SHA256SUMS.sig differ
diff --git a/supported_versions.json b/supported_versions.json
index 0f73716..7999aef 100644
--- a/supported_versions.json
+++ b/supported_versions.json
@@ -11,9 +11,18 @@
     "1.3.9",
     "1.4.6",
     "1.5.7",
-    "1.6.5"
+    "1.6.6",
+    "1.7.5",
+    "1.8.5",
+    "1.9.8",
+    "1.10.3",
+    "1.10.5",
+    "1.11.4",
+    "1.12.2",
+    "1.14.8"
   ],
   "awscli_versions": [
-    "2.14.5"
+    "2.17.4",
+    "2.34.17"
   ]
 }
diff --git a/tests/container-structure-tests.yml.template b/tests/container-structure-tests.yml.template
index 619fc87..fe292c6 100644
--- a/tests/container-structure-tests.yml.template
+++ b/tests/container-structure-tests.yml.template
@@ -11,7 +11,7 @@ commandTests:
   - name: "Check Git version"
     command: "git"
     args: ["--version"]
-    expectedOutput: ["git version 2.39.2"]
+    expectedOutput: ["git version 2.39.5"]
 
   - name: "Check JQ version"
     command: "jq"