diff --git a/app/Models/ApplicationDeploymentQueue.php b/app/Models/ApplicationDeploymentQueue.php
index f16f7f8f96..5bf64b2998 100644
--- a/app/Models/ApplicationDeploymentQueue.php
+++ b/app/Models/ApplicationDeploymentQueue.php
@@ -192,7 +192,7 @@ class ApplicationDeploymentQueue extends Model
             $lockedVars = $lockedVars->merge(
                 $app->environment_variables
                     ->where('is_shown_once', true)
-                    ->pluck('real_value', 'key')
+                    ->flatMap(fn (EnvironmentVariable $variable): array => $variable->logRedactionValues())
                     ->filter()
             );
         }
@@ -201,7 +201,7 @@ class ApplicationDeploymentQueue extends Model
             $lockedVars = $lockedVars->merge(
                 $app->environment_variables_preview
                     ->where('is_shown_once', true)
-                    ->pluck('real_value', 'key')
+                    ->flatMap(fn (EnvironmentVariable $variable): array => $variable->logRedactionValues())
                     ->filter()
             );
         }
diff --git a/app/Models/EnvironmentVariable.php b/app/Models/EnvironmentVariable.php
index e7dd8564bc..176ffee98f 100644
--- a/app/Models/EnvironmentVariable.php
+++ b/app/Models/EnvironmentVariable.php
@@ -309,6 +309,30 @@ class EnvironmentVariable extends BaseModel
         return $real_value;
     }
 
+    /** @return array<int, string> */
+    public function logRedactionValues(): array
+    {
+        $value = $this->real_value;
+        if (! is_string($value) || $value === '') {
+            return [];
+        }
+
+        $values = [$value];
+        if ($this->is_multiline || $this->is_literal) {
+            $unquoted = str_starts_with($value, "'") && str_ends_with($value, "'")
+                ? substr($value, 1, -1)
+                : $value;
+            $values[] = $unquoted;
+            $values[] = escapeBashEnvValue($unquoted);
+            $values[] = str_replace(["\r\n", "\r", "\n"], ['\\n', '\\n', '\\n'], $unquoted);
+            if ($this->is_multiline) {
+                $values = array_merge($values, preg_split('/\r\n|\r|\n/', $unquoted) ?: []);
+            }
+        }
+
+        return array_values(array_unique(array_filter($values, static fn (string $item): bool => $item !== '')));
+    }
+
     public function resolveReferencedValue(): ?string
     {
         $value = $this->value;
diff --git a/app/Traits/ExecuteRemoteCommand.php b/app/Traits/ExecuteRemoteCommand.php
index 87bd7f8748..9b8dd02dfd 100644
--- a/app/Traits/ExecuteRemoteCommand.php
+++ b/app/Traits/ExecuteRemoteCommand.php
@@ -5,6 +5,7 @@ namespace App\Traits;
 use App\Enums\ApplicationDeploymentStatus;
 use App\Exceptions\DeploymentException;
 use App\Helpers\SshMultiplexingHelper;
+use App\Models\EnvironmentVariable;
 use App\Models\Server;
 use Carbon\Carbon;
 use Illuminate\Support\Collection;
@@ -33,7 +34,7 @@ trait ExecuteRemoteCommand
             $lockedVars = $lockedVars->merge(
                 $this->application->environment_variables
                     ->where('is_shown_once', true)
-                    ->pluck('real_value', 'key')
+                    ->flatMap(fn (EnvironmentVariable $variable): array => $variable->logRedactionValues())
                     ->filter()
             );
         }
@@ -42,7 +43,7 @@ trait ExecuteRemoteCommand
             $lockedVars = $lockedVars->merge(
                 $this->application->environment_variables_preview
                     ->where('is_shown_once', true)
-                    ->pluck('real_value', 'key')
+                    ->flatMap(fn (EnvironmentVariable $variable): array => $variable->logRedactionValues())
                     ->filter()
             );
         }
diff --git a/tests/Feature/ApplicationDeploymentControlVarFilteringTest.php b/tests/Feature/ApplicationDeploymentControlVarFilteringTest.php
index e8fb9cb84d..1e76bf58d6 100644
--- a/tests/Feature/ApplicationDeploymentControlVarFilteringTest.php
+++ b/tests/Feature/ApplicationDeploymentControlVarFilteringTest.php
@@ -10,6 +10,7 @@ use App\Models\EnvironmentVariable;
 use App\Models\Project;
 use App\Models\Server;
 use App\Models\Team;
+use App\Models\User;
 use Illuminate\Foundation\Testing\RefreshDatabase;
 use Illuminate\Support\Collection;
 use Illuminate\Support\Facades\DB;
@@ -64,6 +65,75 @@ it('redacts resolved remote secrets from command output', function () {
         ->toBe('token='.REDACTED);
 });
 
+it('does not retain locked values from generated build-time debug logs', function () {
+    config()->set('app.env', 'local');
+    [$application, $server] = makeDeploymentControlVarFixture();
+
+    createApplicationEnvironmentVariable($application, [
+        'key' => 'SINGLE_MARKER',
+        'value' => 'harmless-single-marker',
+        'is_shown_once' => true,
+    ]);
+    createApplicationEnvironmentVariable($application, [
+        'key' => 'MULTILINE_MARKER',
+        'value' => "harmless-first-marker\nharmless-second-marker",
+        'is_multiline' => true,
+        'is_shown_once' => true,
+    ]);
+
+    [$job, $reflection] = makeControlVarFilteringJob($application, $server);
+    invokeDeploymentJobMethod($job, $reflection, 'generate_buildtime_environment_variables');
+
+    $deployment = ApplicationDeploymentQueue::create([
+        'deployment_uuid' => 'harmless-debug-log-deployment',
+        'application_id' => $application->id,
+        'server_id' => $server->id,
+    ]);
+    foreach ($job->recordedLogEntries as $entry) {
+        $deployment->addLogEntry($entry);
+    }
+
+    $retainedLogs = $deployment->fresh()->logs;
+    expect($retainedLogs)
+        ->not->toContain('harmless-single-marker')
+        ->not->toContain('harmless-first-marker')
+        ->not->toContain('harmless-second-marker')
+        ->toContain(REDACTED);
+
+    $member = User::factory()->create();
+    $application->team()->members()->attach($member->id, ['role' => 'member']);
+    $application->settings->update(['is_debug_enabled' => true]);
+    $this->actingAs($member);
+
+    $visibleLines = decode_remote_command_output($deployment->fresh())->pluck('line')->implode("\n");
+    expect($visibleLines)
+        ->toContain('[DEBUG]')
+        ->not->toContain('harmless-first-marker')
+        ->not->toContain('harmless-second-marker');
+});
+
+it('redacts generated multiline forms in remote command and output logging', function () {
+    [$application, $server] = makeDeploymentControlVarFixture();
+    createApplicationEnvironmentVariable($application, [
+        'key' => 'MULTILINE_MARKER',
+        'value' => "harmless-first-marker\nharmless-second-marker",
+        'is_multiline' => true,
+        'is_shown_once' => true,
+    ]);
+
+    [$job, $reflection] = makeControlVarFilteringJob($application, $server);
+    $generated = invokeDeploymentJobMethod($job, $reflection, 'generate_buildtime_environment_variables')
+        ->first(fn (string $line): bool => str_starts_with($line, 'MULTILINE_MARKER='));
+
+    foreach ([$generated, str_replace("\n", '\\n', $generated), 'harmless-second-marker'] as $loggedForm) {
+        $redacted = invokeDeploymentJobMethod($job, $reflection, 'redact_sensitive_info', 'output: '.$loggedForm);
+        expect($redacted)
+            ->not->toContain('harmless-first-marker')
+            ->not->toContain('harmless-second-marker')
+            ->toContain('output: ');
+    }
+});
+
 it('ignores empty and non-string remote secrets when redacting command output', function () {
     [$application, $server] = makeDeploymentControlVarFixture();
     [$job, $reflection] = makeControlVarFilteringJob($application, $server, [