diff --git a/pkgs/by-name/ia/iaito/package.nix b/pkgs/by-name/ia/iaito/package.nix
index f576375c73d6..38cd87da1013 100644
--- a/pkgs/by-name/ia/iaito/package.nix
+++ b/pkgs/by-name/ia/iaito/package.nix
@@ -7,18 +7,21 @@
   python3,
   qt6Packages,
   radare2,
+  xvfb-run,
+  breakpointHook,
+  writableTmpDirAsHomeHook,
   stdenv,
 }:
 stdenv.mkDerivation (finalAttrs: {
   pname = "iaito";
-  version = "6.1.0";
+  version = "6.1.4";
 
   srcs = [
     (fetchFromGitHub {
       owner = "radareorg";
       repo = "iaito";
       tag = finalAttrs.version;
-      hash = "sha256-nvMx0zbfsphfBgxdQnk+EhRpQnJ2Qv05rF7w+zQUUQg=";
+      hash = "sha256-HKh5D96Dwo6YttWcOMlFy4H9OS3FbQvQ5RK+aOY4V5s=";
       name = "main";
     })
     (fetchFromGitHub {
@@ -47,6 +50,7 @@ stdenv.mkDerivation (finalAttrs: {
     python3
     qt6Packages.qttools
     qt6Packages.wrapQtAppsHook
+    breakpointHook
   ];
 
   buildInputs = [
@@ -79,6 +83,22 @@ stdenv.mkDerivation (finalAttrs: {
     runHook postInstall
   '';
 
+  nativeInstallCheckInputs = [
+    xvfb-run
+    writableTmpDirAsHomeHook
+  ];
+
+  # `iaito -v` does only work with GUI access
+  installCheckPhase = ''
+    runHook preCheck
+    xvfb-run -a ${placeholder "out"}/bin/iaito -v | grep "${finalAttrs.version}"
+    runHook postCheck
+  '';
+
+  doInstallCheck = true;
+
+  passthru.updateScript = ./update.sh;
+
   meta = {
     description = "Official radare2 GUI";
     longDescription = ''
diff --git a/pkgs/by-name/ia/iaito/update.sh b/pkgs/by-name/ia/iaito/update.sh
new file mode 100755
index 000000000000..96dfb64c0a32
--- /dev/null
+++ b/pkgs/by-name/ia/iaito/update.sh
@@ -0,0 +1,54 @@
+#!/usr/bin/env nix-shell
+#!nix-shell -i sh -p curl jq nix-prefetch-github coreutils gnused gnugrep
+# shellcheck shell=sh
+set -eu
+
+# Directory of this script / the iaito package
+SCRIPT_DIR="$(readlink -f "$(dirname "$0")")"
+NIXFILE="$SCRIPT_DIR/package.nix"
+
+# Determine latest release version: use $1 if provided, otherwise auto-detect
+if [ -n "${1:-}" ]; then
+    LATEST_VERSION="$1"
+    echo "Using provided iaito version: $LATEST_VERSION"
+else
+    LATEST_VERSION=$(curl -s https://api.github.com/repos/radareorg/iaito/releases/latest | jq -r '.tag_name')
+    echo "Latest iaito version: $LATEST_VERSION"
+fi
+
+CURRENT_VERSION=$(grep 'version = ' "$NIXFILE" | head -1 | sed 's/.*"\(.*\)".*/\1/')
+echo "Current iaito version: $CURRENT_VERSION"
+
+if [ "$LATEST_VERSION" = "$CURRENT_VERSION" ]; then
+    echo "iaito is already up to date"
+    exit 0
+fi
+
+# Update main source version and hash
+echo "Updating main source to $LATEST_VERSION..."
+MAIN_HASH=$(nix-prefetch-github radareorg iaito --rev "$LATEST_VERSION" --json | jq -r '.hash')
+echo "  New main hash: $MAIN_HASH"
+
+sed -i "s|version = \"$CURRENT_VERSION\"|version = \"$LATEST_VERSION\"|" "$NIXFILE"
+sed -i "/repo = \"iaito\";$/,/})/{s|hash = \".*\"|hash = \"$MAIN_HASH\"|}" "$NIXFILE"
+
+# Update translations to latest master revision
+echo "Updating iaito-translations to latest master..."
+LATEST_TRANS_REV=$(curl -s https://api.github.com/repos/radareorg/iaito-translations/commits/master | jq -r '.sha')
+echo "  Latest translations rev: $LATEST_TRANS_REV"
+
+CURRENT_TRANS_REV=$(grep -A3 'repo = "iaito-translations"' "$NIXFILE" | grep 'rev = ' | sed 's/.*"\(.*\)".*/\1/')
+echo "  Current translations rev: $CURRENT_TRANS_REV"
+
+if [ "$LATEST_TRANS_REV" = "$CURRENT_TRANS_REV" ]; then
+    echo "  Translations unchanged"
+else
+    echo "  Updating translations: $CURRENT_TRANS_REV -> $LATEST_TRANS_REV"
+    TRANS_HASH=$(nix-prefetch-github radareorg iaito-translations --rev "$LATEST_TRANS_REV" --json | jq -r '.hash')
+    echo "  New translations hash: $TRANS_HASH"
+
+    sed -i "/repo = \"iaito-translations\"/,/})/{s|rev = \"$CURRENT_TRANS_REV\"|rev = \"$LATEST_TRANS_REV\"|}" "$NIXFILE"
+    sed -i "/repo = \"iaito-translations\"/,/})/{s|hash = \".*\"|hash = \"$TRANS_HASH\"|}" "$NIXFILE"
+fi
+
+echo "Update complete. Please verify with: nix build .#iaito"
diff --git a/pkgs/development/tools/analysis/radare2/default.nix b/pkgs/development/tools/analysis/radare2/default.nix
index 7adc62532e4b..0819a899a1dd 100644
--- a/pkgs/development/tools/analysis/radare2/default.nix
+++ b/pkgs/development/tools/analysis/radare2/default.nix
@@ -21,6 +21,7 @@
   python3,
   readline,
   ruby,
+  versionCheckHook,
   vte,
   xxhash,
   zlib,
@@ -46,19 +47,19 @@ let
   qjs = fetchFromGitHub {
     owner = "quickjs-ng";
     repo = "quickjs";
-    rev = "e2b100e8c5fa7131e9fb22b8a0e9ca0f16eb9892"; # https://github.com/radareorg/radare2/blob/master/subprojects/qjs.wrap
-    hash = "sha256-vq+K93MuvFC+JKw4623gKs53ngw1097l5Kf/RBGU+mA=";
+    rev = "3087a2ce5bcb66cc1fcd9f34d3e5ce3bd43a67d9"; # https://github.com/radareorg/radare2/blob/master/subprojects/qjs.wrap
+    hash = "sha256-Z6DUe/W1+3SYPRPCiL3oNL5ovXCsW3dsFuGkA9WF3W4=";
   };
 in
 stdenv.mkDerivation (finalAttrs: {
   pname = "radare2";
-  version = "6.1.2";
+  version = "6.1.4";
 
   src = fetchFromGitHub {
     owner = "radare";
     repo = "radare2";
     tag = finalAttrs.version;
-    hash = "sha256-YiKbXKKwbeAUkeq4LcUwOxTHU1Hua4YhcwDULiHVmrQ=";
+    hash = "sha256-3MwBtjR3XQMhbJHnD30OVedUEKcje5jDPszNynkGCT8=";
   };
 
   mesonFlags = [
@@ -133,6 +134,12 @@ stdenv.mkDerivation (finalAttrs: {
     install_name_tool -add_rpath $out/lib $out/lib/libr_io.${finalAttrs.version}.dylib
   '';
 
+  nativeInstallCheckInputs = [ versionCheckHook ];
+  versionCheckProgramArg = "-v";
+  doInstallCheck = true;
+
+  passthru.updateScript = ./update.sh;
+
   meta = {
     description = "UNIX-like reverse engineering framework and command-line toolset";
     longDescription = ''
@@ -163,7 +170,7 @@ stdenv.mkDerivation (finalAttrs: {
       mic92
       raskin
     ];
-    mainProgram = "radare2";
+    mainProgram = "r2";
     platforms = lib.platforms.unix;
   };
 })
diff --git a/pkgs/development/tools/analysis/radare2/update.sh b/pkgs/development/tools/analysis/radare2/update.sh
new file mode 100755
index 000000000000..bb9706815776
--- /dev/null
+++ b/pkgs/development/tools/analysis/radare2/update.sh
@@ -0,0 +1,78 @@
+#!/usr/bin/env nix-shell
+#!nix-shell -i sh -p curl jq nix-prefetch-github nix coreutils gnused gnugrep
+# shellcheck shell=sh
+set -eu
+
+# Directory of this script / the radare2 package
+SCRIPT_DIR="$(readlink -f "$(dirname "$0")")"
+NIXFILE="$SCRIPT_DIR/default.nix"
+
+# Determine latest release version
+LATEST_VERSION=$(curl -s https://api.github.com/repos/radareorg/radare2/releases/latest | jq -r '.tag_name')
+echo "Latest radare2 version: $LATEST_VERSION"
+
+CURRENT_VERSION=$(grep 'version = ' "$NIXFILE" | head -1 | sed 's/.*"\(.*\)".*/\1/')
+echo "Current radare2 version: $CURRENT_VERSION"
+
+if [ "$LATEST_VERSION" = "$CURRENT_VERSION" ]; then
+    echo "radare2 is already up to date"
+    exit 0
+fi
+
+# Update main package version and hash
+echo "Updating main source to $LATEST_VERSION..."
+MAIN_HASH=$(nix-prefetch-github radare radare2 --rev "$LATEST_VERSION" --json | jq -r '.hash')
+echo "  New main hash: $MAIN_HASH"
+
+sed -i "s|version = \"$CURRENT_VERSION\"|version = \"$LATEST_VERSION\"|" "$NIXFILE"
+sed -i "/src = fetchFromGitHub/,/};/{s|hash = \".*\"|hash = \"$MAIN_HASH\"|}" "$NIXFILE"
+
+# Update a single subproject
+# Arguments: name owner repo wrap_file ref_type
+update_subproject() {
+    name=$1
+    owner=$2
+    repo=$3
+    wrap_file=$4
+    ref_type=$5
+
+    echo "Checking subproject $name..."
+
+    # Fetch the wrap file from the new version
+    wrap_content=$(curl -sL "https://raw.githubusercontent.com/radareorg/radare2/$LATEST_VERSION/subprojects/$wrap_file")
+    new_rev=$(echo "$wrap_content" | grep '^revision' | sed 's/revision = //')
+
+    # Get the current revision from the nix file
+    current_rev=$(grep -A3 "repo = \"$repo\"" "$NIXFILE" | grep "$ref_type = " | sed 's/.*"\(.*\)".*/\1/')
+
+    if [ "$new_rev" = "$current_rev" ]; then
+        echo "  $name is unchanged at $current_rev"
+        return
+    fi
+
+    echo "  Updating $name: $current_rev -> $new_rev"
+
+    # Prefetch new hash
+    new_hash=$(nix-prefetch-github "$owner" "$repo" --rev "$new_rev" --json | jq -r '.hash')
+    echo "  New hash: $new_hash"
+
+    # Update revision and hash in the nix file
+    sed -i "/repo = \"$repo\"/,/};/{s|$ref_type = \"$current_rev\"|$ref_type = \"$new_rev\"|}" "$NIXFILE"
+    sed -i "/repo = \"$repo\"/,/};/{s|hash = \".*\"|hash = \"$new_hash\"|}" "$NIXFILE"
+}
+
+update_subproject binaryninja Vector35 binaryninja-api binaryninja.wrap rev
+update_subproject sdb radareorg sdb sdb.wrap tag
+update_subproject qjs quickjs-ng quickjs qjs.wrap rev
+
+echo "Update iaito to follow new radare2 version '$LATEST_VERSION'"
+IAITO_UPDATE_SCRIPT="$(readlink -f "$(dirname "$SCRIPT_DIR")/../../../by-name/ia/iaito/update.sh")"
+if "$IAITO_UPDATE_SCRIPT" "$LATEST_VERSION";then
+    echo "iaito updated to $LATEST_VERSION"
+else
+    # iaito release may not have been published yet, release dates are not in sync
+    # sometimes, iaito is released earlier than radare2
+    echo "failed to update iaito to $LATEST_VERSION, continuing"
+fi
+
+echo "Update complete. Please verify with: nix build .#radare2 .#iaito"