diff --git a/app/Jobs/ApplicationDeploymentJob.php b/app/Jobs/ApplicationDeploymentJob.php
index b3f9793c7..04b11b9b4 100644
--- a/app/Jobs/ApplicationDeploymentJob.php
+++ b/app/Jobs/ApplicationDeploymentJob.php
@@ -2779,12 +2779,23 @@ COPY ./nginx.conf /etc/nginx/conf.d/default.conf");
                 $secrets_hash = $this->generate_secrets_hash($variables);
             }
 
-            $this->build_args = $variables->map(function ($value, $key) {
-                $value = escapeshellarg($value);
+            $env_vars = $this->pull_request_id === 0
+                ? $this->application->environment_variables()->where('is_buildtime', true)->get()
+                : $this->application->environment_variables_preview()->where('is_buildtime', true)->get();
 
-                return "--build-arg {$key}={$value}";
+            // Map variables to include is_multiline flag
+            $vars_with_metadata = $variables->map(function ($value, $key) use ($env_vars) {
+                $env = $env_vars->firstWhere('key', $key);
+
+                return [
+                    'key' => $key,
+                    'value' => $value,
+                    'is_multiline' => $env ? $env->is_multiline : false,
+                ];
             });
 
+            $this->build_args = generateDockerBuildArgs($vars_with_metadata);
+
             if ($secrets_hash) {
                 $this->build_args->push("--build-arg COOLIFY_BUILD_SECRETS_HASH={$secrets_hash}");
             }
@@ -2807,14 +2818,17 @@ COPY ./nginx.conf /etc/nginx/conf.d/default.conf");
         }
 
         $secrets_hash = $this->generate_secrets_hash($variables);
-        $env_flags = $variables
-            ->map(function ($env) {
-                $escaped_value = escapeshellarg($env->real_value);
 
-                return "-e {$env->key}={$escaped_value}";
-            })
-            ->implode(' ');
+        // Map to simple array format for the helper function
+        $vars_array = $variables->map(function ($env) {
+            return [
+                'key' => $env->key,
+                'value' => $env->real_value,
+                'is_multiline' => $env->is_multiline,
+            ];
+        });
 
+        $env_flags = generateDockerEnvFlags($vars_array);
         $env_flags .= " -e COOLIFY_BUILD_SECRETS_HASH={$secrets_hash}";
 
         return $env_flags;
diff --git a/bootstrap/helpers/docker.php b/bootstrap/helpers/docker.php
index 1491e4712..af26c97bd 100644
--- a/bootstrap/helpers/docker.php
+++ b/bootstrap/helpers/docker.php
@@ -1119,3 +1119,64 @@ function escapeDollarSign($value)
 
     return str_replace($search, $replace, $value);
 }
+
+/**
+ * Generate Docker build arguments from environment variables collection
+ *
+ * @param  \Illuminate\Support\Collection|array  $variables  Collection of variables with 'key', 'value', and optionally 'is_multiline'
+ * @return \Illuminate\Support\Collection Collection of formatted --build-arg strings
+ */
+function generateDockerBuildArgs($variables): \Illuminate\Support\Collection
+{
+    $variables = collect($variables);
+
+    return $variables->map(function ($var) {
+        $key = is_array($var) ? data_get($var, 'key') : $var->key;
+        $value = is_array($var) ? data_get($var, 'value') : $var->value;
+        $isMultiline = is_array($var) ? data_get($var, 'is_multiline', false) : ($var->is_multiline ?? false);
+
+        if ($isMultiline) {
+            // For multiline variables, strip surrounding quotes and escape for bash
+            $raw_value = trim($value, "'");
+            $escaped_value = str_replace(['\\', '"', '$', '`'], ['\\\\', '\\"', '\\$', '\\`'], $raw_value);
+
+            return "--build-arg {$key}=\"{$escaped_value}\"";
+        }
+
+        // For regular variables, use escapeshellarg for security
+        $value = escapeshellarg($value);
+
+        return "--build-arg {$key}={$value}";
+    });
+}
+
+/**
+ * Generate Docker environment flags from environment variables collection
+ *
+ * @param  \Illuminate\Support\Collection|array  $variables  Collection of variables with 'key', 'value', and optionally 'is_multiline'
+ * @return string Space-separated environment flags
+ */
+function generateDockerEnvFlags($variables): string
+{
+    $variables = collect($variables);
+
+    return $variables
+        ->map(function ($var) {
+            $key = is_array($var) ? data_get($var, 'key') : $var->key;
+            $value = is_array($var) ? data_get($var, 'value') : $var->value;
+            $isMultiline = is_array($var) ? data_get($var, 'is_multiline', false) : ($var->is_multiline ?? false);
+
+            if ($isMultiline) {
+                // For multiline variables, strip surrounding quotes and escape for bash
+                $raw_value = trim($value, "'");
+                $escaped_value = str_replace(['\\', '"', '$', '`'], ['\\\\', '\\"', '\\$', '\\`'], $raw_value);
+
+                return "-e {$key}=\"{$escaped_value}\"";
+            }
+
+            $escaped_value = escapeshellarg($value);
+
+            return "-e {$key}={$escaped_value}";
+        })
+        ->implode(' ');
+}
diff --git a/tests/Feature/MultilineEnvironmentVariableTest.php b/tests/Feature/MultilineEnvironmentVariableTest.php
new file mode 100644
index 000000000..e32a2ce99
--- /dev/null
+++ b/tests/Feature/MultilineEnvironmentVariableTest.php
@@ -0,0 +1,208 @@
+<?php
+
+test('multiline environment variables are properly escaped for docker build args', function () {
+    $sshKey = '-----BEGIN OPENSSH PRIVATE KEY-----
+b3BlbnNzaC1rZXktdjEAAAAABG5vbmUAAAAEbm9uZQAAAAAAAAABAAAAMwAAAAtzc2gtZW
+QyNTUxOQAAACBbhpqHhqv6aI67Mj9abM3DVbmcfYhZAhC7ca4d9UCevAAAAJi/QySHv0Mk
+hwAAAAtzc2gtZWQyNTUxOQAAACBbhpqHhqv6aI67Mj9abM3DVbmcfYhZAhC7ca4d9UCevA
+AAAECBQw4jg1WRT2IGHMncCiZhURCts2s24HoDS0thHnnRKVuGmoeGq/pojrsyP1pszcNV
+uZx9iFkCELtxrh31QJ68AAAAEXNhaWxANzZmZjY2ZDJlMmRkAQIDBA==
+-----END OPENSSH PRIVATE KEY-----';
+
+    $variables = [
+        ['key' => 'SSH_PRIVATE_KEY', 'value' => "'{$sshKey}'", 'is_multiline' => true],
+        ['key' => 'REGULAR_VAR', 'value' => 'simple value', 'is_multiline' => false],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+
+    // SSH key should use double quotes and have proper escaping
+    $sshArg = $buildArgs->first();
+    expect($sshArg)->toStartWith('--build-arg SSH_PRIVATE_KEY="');
+    expect($sshArg)->toEndWith('"');
+    expect($sshArg)->toContain('BEGIN OPENSSH PRIVATE KEY');
+    expect($sshArg)->not->toContain("'BEGIN"); // Should not have the wrapper single quotes
+
+    // Regular var should use escapeshellarg (single quotes)
+    $regularArg = $buildArgs->last();
+    expect($regularArg)->toBe("--build-arg REGULAR_VAR='simple value'");
+});
+
+test('multiline variables with special bash characters are escaped correctly', function () {
+    $valueWithSpecialChars = "line1\nline2 with \"quotes\"\nline3 with \$variables\nline4 with `backticks`";
+
+    $variables = [
+        ['key' => 'SPECIAL_VALUE', 'value' => "'{$valueWithSpecialChars}'", 'is_multiline' => true],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    $arg = $buildArgs->first();
+
+    // Verify double quotes are escaped
+    expect($arg)->toContain('\\"quotes\\"');
+    // Verify dollar signs are escaped
+    expect($arg)->toContain('\\$variables');
+    // Verify backticks are escaped
+    expect($arg)->toContain('\\`backticks\\`');
+});
+
+test('single-line environment variables use escapeshellarg', function () {
+    $variables = [
+        ['key' => 'SIMPLE_VAR', 'value' => 'simple value with spaces', 'is_multiline' => false],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    $arg = $buildArgs->first();
+
+    // Should use single quotes from escapeshellarg
+    expect($arg)->toBe("--build-arg SIMPLE_VAR='simple value with spaces'");
+});
+
+test('multiline certificate with newlines is preserved', function () {
+    $certificate = '-----BEGIN CERTIFICATE-----
+MIIDXTCCAkWgAwIBAgIJAKL0UG+mRkSvMA0GCSqGSIb3DQEBCwUAMEUxCzAJBgNV
+BAYTAkFVMRMwEQYDVQQIDApTb21lLVN0YXRlMSEwHwYDVQQKDBhJbnRlcm5ldCBX
+aWRnaXRzIFB0eSBMdGQwHhcNMTkwOTE3MDUzMzI5WhcNMjkwOTE0MDUzMzI5WjBF
+-----END CERTIFICATE-----';
+
+    $variables = [
+        ['key' => 'TLS_CERT', 'value' => "'{$certificate}'", 'is_multiline' => true],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    $arg = $buildArgs->first();
+
+    // Newlines should be preserved in the output
+    expect($arg)->toContain("\n");
+    expect($arg)->toContain('BEGIN CERTIFICATE');
+    expect($arg)->toContain('END CERTIFICATE');
+    expect(substr_count($arg, "\n"))->toBeGreaterThan(0);
+});
+
+test('multiline JSON configuration is properly escaped', function () {
+    $jsonConfig = '{
+  "key": "value",
+  "nested": {
+    "array": [1, 2, 3]
+  }
+}';
+
+    $variables = [
+        ['key' => 'JSON_CONFIG', 'value' => "'{$jsonConfig}'", 'is_multiline' => true],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    $arg = $buildArgs->first();
+
+    // All double quotes in JSON should be escaped
+    expect($arg)->toContain('\\"key\\"');
+    expect($arg)->toContain('\\"value\\"');
+    expect($arg)->toContain('\\"nested\\"');
+});
+
+test('empty multiline variable is handled correctly', function () {
+    $variables = [
+        ['key' => 'EMPTY_VAR', 'value' => "''", 'is_multiline' => true],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    $arg = $buildArgs->first();
+
+    expect($arg)->toBe('--build-arg EMPTY_VAR=""');
+});
+
+test('multiline variable with only newlines', function () {
+    $onlyNewlines = "\n\n\n";
+
+    $variables = [
+        ['key' => 'NEWLINES_ONLY', 'value' => "'{$onlyNewlines}'", 'is_multiline' => true],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    $arg = $buildArgs->first();
+
+    expect($arg)->toContain("\n");
+    // Should have 3 newlines preserved
+    expect(substr_count($arg, "\n"))->toBe(3);
+});
+
+test('multiline variable with backslashes is escaped correctly', function () {
+    $valueWithBackslashes = "path\\to\\file\nC:\\Windows\\System32";
+
+    $variables = [
+        ['key' => 'PATH_VAR', 'value' => "'{$valueWithBackslashes}'", 'is_multiline' => true],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    $arg = $buildArgs->first();
+
+    // Backslashes should be doubled
+    expect($arg)->toContain('path\\\\to\\\\file');
+    expect($arg)->toContain('C:\\\\Windows\\\\System32');
+});
+
+test('generateDockerEnvFlags produces correct format', function () {
+    $variables = [
+        ['key' => 'NORMAL_VAR', 'value' => 'value', 'is_multiline' => false],
+        ['key' => 'MULTILINE_VAR', 'value' => "'line1\nline2'", 'is_multiline' => true],
+    ];
+
+    $envFlags = generateDockerEnvFlags($variables);
+
+    expect($envFlags)->toContain('-e NORMAL_VAR=');
+    expect($envFlags)->toContain('-e MULTILINE_VAR="');
+    expect($envFlags)->toContain('line1');
+    expect($envFlags)->toContain('line2');
+});
+
+test('helper functions work with collection input', function () {
+    $variables = collect([
+        (object) ['key' => 'VAR1', 'value' => 'value1', 'is_multiline' => false],
+        (object) ['key' => 'VAR2', 'value' => "'multiline\nvalue'", 'is_multiline' => true],
+    ]);
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    expect($buildArgs)->toHaveCount(2);
+
+    $envFlags = generateDockerEnvFlags($variables);
+    expect($envFlags)->toBeString();
+    expect($envFlags)->toContain('-e VAR1=');
+    expect($envFlags)->toContain('-e VAR2="');
+});
+
+test('variables without is_multiline default to false', function () {
+    $variables = [
+        ['key' => 'NO_FLAG_VAR', 'value' => 'some value'],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    $arg = $buildArgs->first();
+
+    // Should use escapeshellarg (single quotes) since is_multiline defaults to false
+    expect($arg)->toBe("--build-arg NO_FLAG_VAR='some value'");
+});
+
+test('real world SSH key example', function () {
+    // Simulate what real_value returns (wrapped in single quotes)
+    $sshKey = "'-----BEGIN OPENSSH PRIVATE KEY-----
+b3BlbnNzaC1rZXktdjEAAAAABG5vbmUAAAAEbm9uZQAAAAAAAAABAAAAMwAAAAtzc2gtZW
+QyNTUxOQAAACBbhpqHhqv6aI67Mj9abM3DVbmcfYhZAhC7ca4d9UCevAAAAJi/QySHv0Mk
+hwAAAAtzc2gtZWQyNTUxOQAAACBbhpqHhqv6aI67Mj9abM3DVbmcfYhZAhC7ca4d9UCevA
+AAAECBQw4jg1WRT2IGHMncCiZhURCts2s24HoDS0thHnnRKVuGmoeGq/pojrsyP1pszcNV
+uZx9iFkCELtxrh31QJ68AAAAEXNhaWxANzZmZjY2ZDJlMmRkAQIDBA==
+-----END OPENSSH PRIVATE KEY-----'";
+
+    $variables = [
+        ['key' => 'KEY', 'value' => $sshKey, 'is_multiline' => true],
+    ];
+
+    $buildArgs = generateDockerBuildArgs($variables);
+    $arg = $buildArgs->first();
+
+    // Should produce clean output without wrapper quotes
+    expect($arg)->toStartWith('--build-arg KEY="-----BEGIN OPENSSH PRIVATE KEY-----');
+    expect($arg)->toEndWith('-----END OPENSSH PRIVATE KEY-----"');
+    // Should NOT have the escaped quote sequence that was in the bug
+    expect($arg)->not->toContain("''");
+    expect($arg)->not->toContain("'\\''");
+});