diff --git a/robot/cli_plan_context_commands.robot b/robot/cli_plan_context_commands.robot
index de53b8690..519ce006c 100644
--- a/robot/cli_plan_context_commands.robot
+++ b/robot/cli_plan_context_commands.robot
@@ -19,7 +19,7 @@ Initialize New Project
     [Setup]    Setup Test Directory
 
     ${result}=    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}
-    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_AUTO_APPLY_MIGRATIONS=true    stderr=STDOUT    timeout=30s
+    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_AUTO_APPLY_MIGRATIONS=true    stderr=STDOUT    timeout=60s
 
     Should Be Equal As Integers    ${result.rc}    0    Init failed: ${result.stdout}
     Should Exist    ${TEST_DIR}${/}.cleveragents
@@ -55,7 +55,7 @@ Create Plan With Tell
     [Setup]    Initialize Test Project
 
     ${result}=    Run Process    ${PYTHON}    -m    cleveragents    tell    Add error handling
-    ...    cwd=${TEST_DIR}    timeout=30s
+    ...    cwd=${TEST_DIR}    timeout=60s
 
     Should Be Equal As Integers    ${result.rc}    0
 
@@ -72,7 +72,7 @@ Build Plan
     [Setup]    Initialize Test Project With Plan
 
     ${result}=    Run Process    ${PYTHON}    -m    cleveragents    build
-    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=30s
+    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=60s
 
     Should Be Equal As Integers    ${result.rc}    0
 
@@ -83,7 +83,7 @@ Apply Plan Changes
     [Setup]    Initialize Test Project With Built Plan
 
     ${result}=    Run Process    ${PYTHON}    -m    cleveragents    apply    --yes
-    ...    cwd=${TEST_DIR}    timeout=30s
+    ...    cwd=${TEST_DIR}    timeout=60s
 
     Should Be Equal As Integers    ${result.rc}    0
 
@@ -219,7 +219,7 @@ Clear All Context
     [Setup]    Initialize Test Project With Context
 
     ${result}=    Run Process    ${PYTHON}    -m    cleveragents    context    clear    --yes
-    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_AUTO_APPLY_MIGRATIONS=true    stderr=STDOUT    timeout=30s
+    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_AUTO_APPLY_MIGRATIONS=true    stderr=STDOUT    timeout=60s
 
     Should Be Equal As Integers    ${result.rc}    0    Context clear failed: ${result.stdout}
 
@@ -266,14 +266,14 @@ Initialize Test Project With Plan
     [Documentation]    Initialize project and create a plan
     Initialize Test Project
     ${result}=    Run Process    ${PYTHON}    -m    cleveragents    tell    Test instruction
-    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=30s
+    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=60s
     Should Be Equal As Integers    ${result.rc}    0
 
 Initialize Test Project With Built Plan
     [Documentation]    Initialize project with a built plan
     Initialize Test Project With Plan
     ${result}=    Run Process    ${PYTHON}    -m    cleveragents    build
-    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=30s
+    ...    cwd=${TEST_DIR}    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=60s
     Should Be Equal As Integers    ${result.rc}    0
 
 Initialize Test Project With Multiple Plans
diff --git a/robot/core_cli_commands.robot b/robot/core_cli_commands.robot
index d6e83dfcd..d3eb9f3d5 100644
--- a/robot/core_cli_commands.robot
+++ b/robot/core_cli_commands.robot
@@ -16,7 +16,7 @@ ${PROJECT_NAME}   test-project
 *** Test Cases ***
 Test CLI Help Shows All Commands
     [Documentation]    Verify that CLI help displays all expected command groups
-    ${result} =    Run Process    ${PYTHON}    -m    cleveragents    --help    timeout=30s
+    ${result} =    Run Process    ${PYTHON}    -m    cleveragents    --help    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    AI-powered development assistant
     Should Contain    ${result.stdout}    project
@@ -31,7 +31,7 @@ Test Project Initialization
     [Documentation]    Test initializing a new CleverAgents project
     Create Directory    ${TEST_DIR}/project1
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}
-    ...    cwd=${TEST_DIR}/project1    timeout=30s
+    ...    cwd=${TEST_DIR}/project1    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Project '${PROJECT_NAME}' initialized successfully
     Directory Should Exist    ${TEST_DIR}/project1/.cleveragents
@@ -44,9 +44,9 @@ Test Project Initialization
 Test Project Cannot Initialize Twice
     [Documentation]    Verify project cannot be initialized twice without force
     Create Directory    ${TEST_DIR}/project2
-    Run Process    ${PYTHON}    -m    cleveragents    init    first-project    cwd=${TEST_DIR}/project2    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    first-project    cwd=${TEST_DIR}/project2    timeout=60s
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    init    second-project
-    ...    cwd=${TEST_DIR}/project2    timeout=30s
+    ...    cwd=${TEST_DIR}/project2    timeout=60s
     Should Not Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stderr}    Project already initialized
     Should Contain    ${result.stderr}    --force
@@ -54,19 +54,19 @@ Test Project Cannot Initialize Twice
 Test Force Reinitialize Project
     [Documentation]    Test force reinitialization of a project
     Create Directory    ${TEST_DIR}/project3
-    Run Process    ${PYTHON}    -m    cleveragents    init    first-project    cwd=${TEST_DIR}/project3    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    first-project    cwd=${TEST_DIR}/project3    timeout=60s
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    init    second-project    --force
-    ...    cwd=${TEST_DIR}/project3    timeout=30s
+    ...    cwd=${TEST_DIR}/project3    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Project 'second-project' initialized successfully
 
 Test Context Add Files
     [Documentation]    Test adding files to context
     Create Directory    ${TEST_DIR}/project4
-    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project4    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project4    timeout=60s
     Create File    ${TEST_DIR}/project4/test.py    print('hello world')
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    context    add    test.py
-    ...    cwd=${TEST_DIR}/project4    timeout=30s
+    ...    cwd=${TEST_DIR}/project4    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Added 1 file(s) to context
     Should Contain    ${result.stdout}    test.py
@@ -74,13 +74,13 @@ Test Context Add Files
 Test Context List Files
     [Documentation]    Test listing context files
     Create Directory    ${TEST_DIR}/project5
-    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project5    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project5    timeout=60s
     Create File    ${TEST_DIR}/project5/file1.py    # File 1
     Create File    ${TEST_DIR}/project5/file2.py    # File 2
     Run Process    ${PYTHON}    -m    cleveragents    context    add    file1.py    file2.py
-    ...    cwd=${TEST_DIR}/project5    timeout=30s
+    ...    cwd=${TEST_DIR}/project5    timeout=60s
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    context    list
-    ...    cwd=${TEST_DIR}/project5    timeout=30s
+    ...    cwd=${TEST_DIR}/project5    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    file1.py
     Should Contain    ${result.stdout}    file2.py
@@ -88,20 +88,20 @@ Test Context List Files
 Test Context Clear
     [Documentation]    Test clearing context files
     Create Directory    ${TEST_DIR}/project6
-    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project6    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project6    timeout=60s
     Create File    ${TEST_DIR}/project6/test.py    # Test file
-    Run Process    ${PYTHON}    -m    cleveragents    context    add    test.py    cwd=${TEST_DIR}/project6    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    context    add    test.py    cwd=${TEST_DIR}/project6    timeout=60s
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    context    clear    --yes
-    ...    cwd=${TEST_DIR}/project6    timeout=30s
+    ...    cwd=${TEST_DIR}/project6    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Cleared all files from context
 
 Test Plan Creation With Tell
     [Documentation]    Test creating a plan using tell command
     Create Directory    ${TEST_DIR}/project7
-    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project7    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project7    timeout=60s
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    tell    Add error handling to main function
-    ...    cwd=${TEST_DIR}/project7    timeout=30s
+    ...    cwd=${TEST_DIR}/project7    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Plan created
     Should Contain    ${result.stdout}    error handling
@@ -109,10 +109,10 @@ Test Plan Creation With Tell
 Test Plan Build
     [Documentation]    Test building a plan
     Create Directory    ${TEST_DIR}/project8
-    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project8    timeout=30s
-    Run Process    ${PYTHON}    -m    cleveragents    tell    Create example code    cwd=${TEST_DIR}/project8    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project8    timeout=60s
+    Run Process    ${PYTHON}    -m    cleveragents    tell    Create example code    cwd=${TEST_DIR}/project8    timeout=60s
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    build    cwd=${TEST_DIR}/project8
-    ...    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=30s
+    ...    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Plan built successfully
     Should Contain    ${result.stdout}    Generated
@@ -121,11 +121,11 @@ Test Plan Build
 Test Plan Apply
     [Documentation]    Test applying plan changes
     Create Directory    ${TEST_DIR}/project9
-    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project9    timeout=30s
-    Run Process    ${PYTHON}    -m    cleveragents    tell    Create example file    cwd=${TEST_DIR}/project9    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project9    timeout=60s
+    Run Process    ${PYTHON}    -m    cleveragents    tell    Create example file    cwd=${TEST_DIR}/project9    timeout=60s
     Run Process    ${PYTHON}    -m    cleveragents    build    cwd=${TEST_DIR}/project9
-    ...    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=30s
-    ${result} =    Run Process    ${PYTHON}    -m    cleveragents    apply    --yes    cwd=${TEST_DIR}/project9    timeout=30s
+    ...    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=60s
+    ${result} =    Run Process    ${PYTHON}    -m    cleveragents    apply    --yes    cwd=${TEST_DIR}/project9    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Successfully applied
     File Should Exist    ${TEST_DIR}/project9/example.py
@@ -133,21 +133,21 @@ Test Plan Apply
 Test Plan List
     [Documentation]    Test listing plans
     Create Directory    ${TEST_DIR}/project10
-    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project10    timeout=30s
-    Run Process    ${PYTHON}    -m    cleveragents    tell    First plan    cwd=${TEST_DIR}/project10    timeout=30s
-    Run Process    ${PYTHON}    -m    cleveragents    plan    new    second-plan    cwd=${TEST_DIR}/project10    timeout=30s
-    ${result} =    Run Process    ${PYTHON}    -m    cleveragents    plan    list    cwd=${TEST_DIR}/project10    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project10    timeout=60s
+    Run Process    ${PYTHON}    -m    cleveragents    tell    First plan    cwd=${TEST_DIR}/project10    timeout=60s
+    Run Process    ${PYTHON}    -m    cleveragents    plan    new    second-plan    cwd=${TEST_DIR}/project10    timeout=60s
+    ${result} =    Run Process    ${PYTHON}    -m    cleveragents    plan    list    cwd=${TEST_DIR}/project10    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Plans (3 total)
 
 Test Shortcut Commands Work
     [Documentation]    Test that shortcut commands work properly
     Create Directory    ${TEST_DIR}/project11
-    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project11    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    ${PROJECT_NAME}    cwd=${TEST_DIR}/project11    timeout=60s
     Create File    ${TEST_DIR}/project11/test.txt    Test content
     # Test context-load shortcut
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    context-load    test.txt
-    ...    cwd=${TEST_DIR}/project11    timeout=30s
+    ...    cwd=${TEST_DIR}/project11    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Added 1 file(s) to context
 
@@ -156,30 +156,30 @@ Test End To End Workflow
     Create Directory    ${TEST_DIR}/project12
     # Initialize project
     ${init} =    Run Process    ${PYTHON}    -m    cleveragents    init    workflow-project
-    ...    cwd=${TEST_DIR}/project12    timeout=30s
+    ...    cwd=${TEST_DIR}/project12    timeout=60s
     Should Be Equal As Numbers    ${init.rc}    0
     # Add context
     Create File    ${TEST_DIR}/project12/input.py    def main(): pass
     ${add} =    Run Process    ${PYTHON}    -m    cleveragents    context    add    input.py
-    ...    cwd=${TEST_DIR}/project12    timeout=30s
+    ...    cwd=${TEST_DIR}/project12    timeout=60s
     Should Be Equal As Numbers    ${add.rc}    0
     # Create plan
     ${tell} =    Run Process    ${PYTHON}    -m    cleveragents    tell    Add logging to main function
-    ...    cwd=${TEST_DIR}/project12    timeout=30s
+    ...    cwd=${TEST_DIR}/project12    timeout=60s
     Should Be Equal As Numbers    ${tell.rc}    0
     # Build plan
     ${build} =    Run Process    ${PYTHON}    -m    cleveragents    build    cwd=${TEST_DIR}/project12
-    ...    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=30s
+    ...    env:CLEVERAGENTS_TESTING_USE_MOCK_AI=true    timeout=60s
     Should Be Equal As Numbers    ${build.rc}    0
     # Apply changes
-    ${apply} =    Run Process    ${PYTHON}    -m    cleveragents    apply    --yes    cwd=${TEST_DIR}/project12    timeout=30s
+    ${apply} =    Run Process    ${PYTHON}    -m    cleveragents    apply    --yes    cwd=${TEST_DIR}/project12    timeout=60s
     Should Be Equal As Numbers    ${apply.rc}    0
     # Verify file created
     File Should Exist    ${TEST_DIR}/project12/example.py
 
 Test Command Error Handling
     [Documentation]    Test error handling for invalid commands
-    ${result} =    Run Process    ${PYTHON}    -m    cleveragents    invalid-command    timeout=30s
+    ${result} =    Run Process    ${PYTHON}    -m    cleveragents    invalid-command    timeout=60s
     Should Not Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stderr}    Invalid command
 
@@ -187,16 +187,16 @@ Test Project Status Without Project
     [Documentation]    Test project status command without initialized project
     Create Directory    ${TEST_DIR}/no_project
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    project    status
-    ...    cwd=${TEST_DIR}/no_project    timeout=30s
+    ...    cwd=${TEST_DIR}/no_project    timeout=60s
     Should Not Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stderr}    No project found
 
 Test Project Status With Project
     [Documentation]    Test project status command with initialized project
     Create Directory    ${TEST_DIR}/with_project
-    Run Process    ${PYTHON}    -m    cleveragents    init    status-test    cwd=${TEST_DIR}/with_project    timeout=30s
+    Run Process    ${PYTHON}    -m    cleveragents    init    status-test    cwd=${TEST_DIR}/with_project    timeout=60s
     ${result} =    Run Process    ${PYTHON}    -m    cleveragents    project    status
-    ...    cwd=${TEST_DIR}/with_project    timeout=30s
+    ...    cwd=${TEST_DIR}/with_project    timeout=60s
     Should Be Equal As Numbers    ${result.rc}    0
     Should Contain    ${result.stdout}    Project: status-test
     Should Contain    ${result.stdout}    Plans: 1
diff --git a/robot/database_integration.robot b/robot/database_integration.robot
index b0e743de6..cfc5bc755 100644
--- a/robot/database_integration.robot
+++ b/robot/database_integration.robot
@@ -755,7 +755,7 @@ Run Python Script
     # Write to a temporary file
     ${temp_file}=    Evaluate    __import__('tempfile').NamedTemporaryFile(mode='w', suffix='.py', delete=False, dir='/tmp').name
     Create File    ${temp_file}    ${full_code}
-    ${result}=    Run Process    ${PYTHON}    ${temp_file}    timeout=10s    stderr=STDOUT    env:PYTHONWARNINGS=ignore    env:PYTHONDONTWRITEBYTECODE=1
+    ${result}=    Run Process    ${PYTHON}    ${temp_file}    timeout=60s    stderr=STDOUT    env:PYTHONWARNINGS=ignore    env:PYTHONDONTWRITEBYTECODE=1
     Remove File    ${temp_file}
     # Check if process failed and log stderr if present
     IF    ${result.rc} != 0