diff --git a/src/Agent/BaseCodingAgent.php b/src/Agent/BaseCodingAgent.php
index bcb9aca..d2bac2e 100644
--- a/src/Agent/BaseCodingAgent.php
+++ b/src/Agent/BaseCodingAgent.php
@@ -6,6 +6,7 @@
 
 use EtfsCodingAgent\Service\WorkspaceToolingServiceInterface;
 use NeuronAI\Agent;
+use NeuronAI\Exceptions\ToolMaxTriesException;
 use NeuronAI\Observability\Events\AgentError;
 use NeuronAI\Observability\Events\ToolCalled;
 use NeuronAI\Observability\Events\ToolCalling;
@@ -282,9 +283,30 @@ protected function tools(): array
     /**
      * Override to catch tool execution errors and return them as results instead of crashing.
      * This allows the agent to learn from its mistakes and retry with correct parameters.
+     *
+     * Also tracks tool invocation attempts and enforces a maximum retry limit
+     * (via ToolMaxTriesException) to prevent infinite tool-call loops — e.g. when
+     * context-window trimming causes the agent to lose its conversation state.
+     *
+     * @see https://github.com/dx-tooling/sitebuilder-webapp/issues/75
+     *
+     * @throws ToolMaxTriesException
      */
     protected function executeSingleTool(ToolInterface $tool): void
     {
+        $this->toolAttempts[$tool->getName()] = ($this->toolAttempts[$tool->getName()] ?? 0) + 1;
+
+        $maxTries = $tool->getMaxTries() ?? $this->toolMaxTries;
+
+        if ($this->toolAttempts[$tool->getName()] > $maxTries) {
+            $exception = new ToolMaxTriesException(
+                "Tool {$tool->getName()} has been attempted too many times: {$maxTries} attempts."
+            );
+            $this->notify('error', new AgentError($exception));
+
+            throw $exception;
+        }
+
         $this->notify('tool-calling', new ToolCalling($tool));
 
         try {
diff --git a/tests/Unit/Agent/BaseCodingAgentTest.php b/tests/Unit/Agent/BaseCodingAgentTest.php
index 999f042..4199eb2 100644
--- a/tests/Unit/Agent/BaseCodingAgentTest.php
+++ b/tests/Unit/Agent/BaseCodingAgentTest.php
@@ -4,6 +4,7 @@
 
 use EtfsCodingAgent\Agent\BaseCodingAgent;
 use EtfsCodingAgent\Service\WorkspaceToolingServiceInterface;
+use NeuronAI\Exceptions\ToolMaxTriesException;
 use NeuronAI\Tools\PropertyType;
 use NeuronAI\Tools\Tool;
 use NeuronAI\Tools\ToolProperty;
@@ -127,3 +128,67 @@ public function runShellCommand(string $workingDirectory, string $command): stri
     expect($result)->toContain('required');
     expect($result)->toContain('optional');
 });
+
+it('throws ToolMaxTriesException when a tool exceeds max attempts', function () {
+    $mockFacade = createMockFacade();
+    $agent      = new BaseCodingAgent($mockFacade);
+
+    // Default toolMaxTries is 5
+    $tool = Tool::make('test_tool', 'A test tool')
+        ->setCallable(fn (): string => 'ok');
+
+    $reflection = new ReflectionMethod($agent, 'executeSingleTool');
+
+    // Execute 5 times — should succeed
+    for ($i = 0; $i < 5; $i++) {
+        $reflection->invoke($agent, $tool);
+    }
+
+    expect($tool->getResult())->toBe('ok');
+
+    // 6th attempt should throw
+    $reflection->invoke($agent, $tool);
+})->throws(ToolMaxTriesException::class, 'too many times');
+
+it('tracks tool attempts per tool name independently', function () {
+    $mockFacade = createMockFacade();
+    $agent      = new BaseCodingAgent($mockFacade);
+
+    $toolA = Tool::make('tool_a', 'Tool A')->setCallable(fn (): string => 'a');
+    $toolB = Tool::make('tool_b', 'Tool B')->setCallable(fn (): string => 'b');
+
+    $reflection = new ReflectionMethod($agent, 'executeSingleTool');
+
+    // Execute tool_a 4 times (under limit of 5)
+    for ($i = 0; $i < 4; $i++) {
+        $reflection->invoke($agent, $toolA);
+    }
+
+    // Execute tool_b 4 times (under limit of 5) — should not be affected by tool_a's count
+    for ($i = 0; $i < 4; $i++) {
+        $reflection->invoke($agent, $toolB);
+    }
+
+    expect($toolA->getResult())->toBe('a');
+    expect($toolB->getResult())->toBe('b');
+});
+
+it('catches tool execution errors and sets them as result without affecting attempt tracking', function () {
+    $mockFacade = createMockFacade();
+    $agent      = new BaseCodingAgent($mockFacade);
+
+    $callCount = 0;
+    $tool      = Tool::make('flaky_tool', 'A flaky tool')
+        ->setCallable(function () use (&$callCount): string {
+            $callCount++;
+            throw new RuntimeException('Flaky error');
+        });
+
+    $reflection = new ReflectionMethod($agent, 'executeSingleTool');
+
+    // Execute — should catch the error and set it as result
+    $reflection->invoke($agent, $tool);
+
+    expect($tool->getResult())->toContain('Flaky error');
+    expect($callCount)->toBe(1);
+});