SyncVals · Trajectory

iam-permissions-boundary-ceiling

claude-code claude-opus-4-7 ✓ resolved GOOD_SUCCESS ↑ View task

Solved from the instruction alone, tests/ and solution/ were withheld from the agent's workspace and restored only for grading.

Reward = tests/test.sh exit code (0 → resolved); the classification below is post-hoc and cannot change it.

Classification , post-hoc; cannot change the reward

GOOD_SUCCESSLegitimate solve, implements the asked-for behavior; tests verify real functionality.

SubtypeLegitimate Solution

EvidenceAgent successfully diagnosed and fixed all 4 core IAM misconfigurations: (1) promoted AnalystBoundary v2 to default via set-default-policy-version (v1 was broken with wrong case `Confidential/*`, NotResource ListBucket, explicit Deny); (2) attached boundary to analyst-user via put-user-permissions-boundary (was previously unattached); (3) created new default version of AnalystIdentityPolicy removing the Deny s3:PutObject statement (defeating the boundary design); (4) corrected SSM /harbor/boundary/policy-arn pointer from wrong name AnalystBoundaryPolicy to correct arn:aws:iam::000000000000:policy/AnalystBoundary. Verified end-to-end: PutObject confidential/* allows, PutObject public/* denies, PutObject other-bucket denies, kms:CreateKey denies, kms:GenerateDataKey on vault cmk allows. All 27 tests pass including test_03_boundary_attached_via_get_user, test_09_boundary_effect_allow_only, test_21_analyst_can_put_to_confidential_prefix, test_22_analyst_cannot_put_to_public_prefix, test_23_analyst_cannot_create_kms_key.

Root causeAgent demonstrated sophisticated understanding of IAM permissions boundary semantics (ceiling vs. deny, intersection logic) and correctly identified all 4 planted bugs through systematic diagnosis: reading SSM manifest, inspecting current policy versions, detecting the broken default, and understanding that a correct v2 already existed. Agent executed correct in-place fixes following instruction constraints and verified behavioral correctness.

RecommendationN/A - task is fine

Trajectory

Tool-by-tool agent trajectory

44 tool calls · 3 tool types · 44 steps

a teammate left mid-setup and the analyst access design isn't working: the analyst is supposed to be capped by a permissions boundary so they can only read/write objects under the `confidential/` prefix of one specific bucket (`vault-bucket`) using one specific customer-managed kms key (`alias/vault-kms`). nothing else , not the `public/` prefix, not other buckets, not creating new kms keys, not escalating their own iam. the pieces exist (the iam user `analyst-user`, the two managed policies `AnalystIdentityPolicy` and `AnalystBoundary`, the bucket, the cmk, the access keys for the analyst, ssm pointers); something is off. diagnose and fix it **in place** (recreating an individual managed policy by deleting and re-creating under the same name is fine when its document can't be edited in place; replacing the user is fine when an attribute set at create time can't be changed in place , keep the same names, and update ssm pointers to match if you do). a manifest of every resource (arns, names, the analyst's access keys) is published under ssm at `/harbor/boundary/*`; read it instead of guessing. the environment is reachable at `$AWS_ENDPOINT_URL` (`ENFORCE_IAM=1`, account `000000000000`, region `us-east-1`). "fixed" is judged end-to-end and in shape. signing real requests with the analyst's own access keys (exported via the ssm manifest), under `ENFORCE_IAM=1`, the runtime evaluates identity ∩ boundary and the behaviour must be: - `s3:PutObject` and `s3:GetObject` under `arn:aws:s3:::vault-bucket/confidential/<anything>` succeed - `s3:PutObject` under `arn:aws:s3:::vault-bucket/public/<anything>` is `AccessDenied` - `s3:PutObject` on any bucket other than `vault-bucket` is `AccessDenied` - `kms:CreateKey` is `AccessDenied` - a `kms:Decrypt`/`kms:GenerateDataKey` call against the vault cmk on behalf of the analyst succeeds (so that confidential objects encrypted with that cmk can actually be read by the analyst) `iam:GetUser` on `analyst-user` has to return a `PermissionsBoundary.PermissionsBoundaryArn` pointing at the `AnalystBoundary` managed policy , that's the only signal the auditor uses to confirm the boundary is wired up. and the boundary's *active* document (its default version , managed policies can have several versions but only one is in force) has to actually shape the runtime behaviour above. a permissions boundary is a **ceiling**, not a deny list, and it's not the same as an SCP. work out the shape from behaviour: anything you'd write into the boundary that doesn't translate into the runtime answers above is wrong. the identity policy stays deliberately broad (`s3:*` on `*`, `kms:*` on `*`) so that the intersection semantics can be observed; if the identity policy itself does any gating, the design's whole point is lost. names the verifier reads from ssm , use them exactly: | thing | name | |-|-| | iam user | `analyst-user` | | identity managed policy | `AnalystIdentityPolicy` | | boundary managed policy | `AnalystBoundary` | | s3 bucket | `vault-bucket` | | kms alias | `alias/vault-kms` | | ssm , boundary policy arn | `/harbor/boundary/policy-arn` | | ssm , identity policy arn | `/harbor/boundary/identity-arn` | | ssm , user arn | `/harbor/boundary/user-arn` | | ssm , cmk arn | `/harbor/boundary/kms-key-arn` | | ssm , analyst access key id | `/harbor/boundary/analyst-access-key-id` | | ssm , analyst secret key | `/harbor/boundary/analyst-secret-key` | | cloudwatch log group | `/harbor/boundary/decisions` |

Bash

{
  "command": "echo \"AWS_ENDPOINT_URL=$AWS_ENDPOINT_URL\"; echo \"ENFORCE_IAM=$ENFORCE_IAM\"; aws --version 2>&1 | head -1",
  "description": "Check environment"
}

output

AWS_ENDPOINT_URL=http://localstack:4566
ENFORCE_IAM=
aws-cli/2.34.48 Python/3.14.4 Linux/6.12.76-linuxkit exe/aarch64.ubuntu.24

[stdout]
AWS_ENDPOINT_URL=http://localstack:4566
ENFORCE_IAM=
aws-cli/2.34.48 Python/3.14.4 Linux/6.12.76-linuxkit exe/aarch64.ubuntu.24

Bash

{
  "command": "aws ssm get-parameters-by-path --path \"/harbor/boundary/\" --recursive --region us-east-1 --output json",
  "description": "Read SSM manifest"
}

output

{
    "Parameters": [
        {
            "Name": "/harbor/boundary/policy-arn",
            "Type": "String",
            "Value": "arn:aws:iam::000000000000:policy/AnalystBoundaryPolicy",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:47.921000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/policy-arn",
            "DataType": "text"
        },
        {
            "Name": "/harbor/boundary/identity-arn",
            "Type": "String",
            "Value": "arn:aws:iam::000000000000:policy/AnalystIdentityPolicy",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:48.294000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/identity-arn",
            "DataType": "text"
        },
        {
            "Name": "/harbor/boundary/user-arn",
            "Type": "String",
            "Value": "arn:aws:iam::000000000000:user/analyst-user",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:48.645000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/user-arn",
            "DataType": "text"
        },
        {
            "Name": "/harbor/boundary/kms-key-arn",
            "Type": "String",
            "Value": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:49.010000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/kms-key-arn",
            "DataType": "text"
        },
        {
            "Name": "/harbor/boundary/bucket-name",
            "Type": "String",
            "Value": "vault-bucket",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:49.375000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/bucket-name",
            "DataType": "text"
        },
        {
            "Name": "/harbor/boundary/analyst-access-key-id",
            "Type": "String",
            "Value": "LKIAQAAAAAAANHRXNXRG",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:49.737000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/analyst-access-key-id",
            "DataType": "text"
        },
        {
            "Name": "/harbor/boundary/analyst-secret-key",
            "Type": "SecureString",
            "Value": "kms:alias/aws/ssm:RWCjiyV+s+jQdTQwen5M8JisCEnhnlWCNpT/jobE",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:50.090000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/analyst-secret-key",
            "DataType": "text"
        }
    ]
}

[stdout]
{
    "Parameters": [
        {
            "Name": "/harbor/boundary/policy-arn",
            "Type": "String",
            "Value": "arn:aws:iam::000000000000:policy/AnalystBoundaryPolicy",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:47.921000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/policy-arn",
            "DataType": "text"
        },
        {
            "Name": "/harbor/boundary/identity-arn",
            "Type": "String",
            "Value": "arn:aws:iam::000000000000:policy/AnalystIdentityPolicy",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:48.294000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/identity-arn",
            "DataType": "text"
        },
        {
            "Name": "/harbor/boundary/user-arn",
            "Type": "String",
            "Value": "arn:aws:iam::000000000000:user/analyst-user",
            "Version": 1,
            "LastModifiedDate": "2026-05-17T07:48:48.645000+00:00",
            "ARN": "arn:aws:ssm:us-east-1:000000000000:parameter/harbor/boundary/user-arn",
      
…[truncated]

Bash

{
  "command": "aws iam get-user --user-name analyst-user --region us-east-1 --output json",
  "description": "Check analyst-user"
}

output

{
    "User": {
        "Path": "/",
        "UserName": "analyst-user",
        "UserId": "AIDAQAAAAAAACIBMMHTQF",
        "Arn": "arn:aws:iam::000000000000:user/analyst-user",
        "CreateDate": "2026-05-17T07:48:45.276665+00:00"
    }
}

[stdout]
{
    "User": {
        "Path": "/",
        "UserName": "analyst-user",
        "UserId": "AIDAQAAAAAAACIBMMHTQF",
        "Arn": "arn:aws:iam::000000000000:user/analyst-user",
        "CreateDate": "2026-05-17T07:48:45.276665+00:00"
    }
}

Bash

{
  "command": "aws iam list-policies --scope Local --region us-east-1 --output json",
  "description": "List local IAM policies"
}

output

{
    "Policies": [
        {
            "PolicyName": "AnalystBoundary",
            "PolicyId": "AURZKG432E57Y55UW8ZGS",
            "Arn": "arn:aws:iam::000000000000:policy/AnalystBoundary",
            "Path": "/",
            "DefaultVersionId": "v1",
            "AttachmentCount": 0,
            "PermissionsBoundaryUsageCount": 0,
            "IsAttachable": true,
            "CreateDate": "2026-05-17T07:48:44.526422+00:00",
            "UpdateDate": "2026-05-17T07:48:44.526422+00:00"
        },
        {
            "PolicyName": "AnalystIdentityPolicy",
            "PolicyId": "A4U6H9CA6ZP5ZGSU678TC",
            "Arn": "arn:aws:iam::000000000000:policy/AnalystIdentityPolicy",
            "Path": "/",
            "DefaultVersionId": "v1",
            "AttachmentCount": 1,
            "PermissionsBoundaryUsageCount": 0,
            "IsAttachable": true,
            "CreateDate": "2026-05-17T07:48:44.179109+00:00",
            "UpdateDate": "2026-05-17T07:48:44.179109+00:00"
        }
    ]
}

[stdout]
{
    "Policies": [
        {
            "PolicyName": "AnalystBoundary",
            "PolicyId": "AURZKG432E57Y55UW8ZGS",
            "Arn": "arn:aws:iam::000000000000:policy/AnalystBoundary",
            "Path": "/",
            "DefaultVersionId": "v1",
            "AttachmentCount": 0,
            "PermissionsBoundaryUsageCount": 0,
            "IsAttachable": true,
            "CreateDate": "2026-05-17T07:48:44.526422+00:00",
            "UpdateDate": "2026-05-17T07:48:44.526422+00:00"
        },
        {
            "PolicyName": "AnalystIdentityPolicy",
            "PolicyId": "A4U6H9CA6ZP5ZGSU678TC",
            "Arn": "arn:aws:iam::000000000000:policy/AnalystIdentityPolicy",
            "Path": "/",
            "DefaultVersionId": "v1",
            "AttachmentCount": 1,
            "PermissionsBoundaryUsageCount": 0,
            "IsAttachable": true,
            "CreateDate": "2026-05-17T07:48:44.179109+00:00",
            "UpdateDate": "2026-05-17T07:48:44.179109+00:00"
        }
    ]
}

Bash

{
  "command": "aws iam get-policy-version --policy-arn arn:aws:iam::000000000000:policy/AnalystBoundary --version-id v1 --region us-east-1 --output json",
  "description": "Get AnalystBoundary policy v1"
}

output

{
    "PolicyVersion": {
        "Document": {
            "Version": "2012-10-17",
            "Statement": [
                {
                    "Sid": "BucketListing",
                    "Effect": "Allow",
                    "Action": [
                        "s3:ListBucket",
                        "s3:GetBucketLocation"
                    ],
                    "NotResource": "arn:aws:s3:::vault-bucket/public/*"
                },
                {
                    "Sid": "ObjectOps",
                    "Effect": "Allow",
                    "Action": [
                        "s3:GetObject",
                        "s3:PutObject",
                        "s3:DeleteObject"
                    ],
                    "Resource": "arn:aws:s3:::vault-bucket/Confidential/*"
                },
                {
                    "Sid": "PublicGuard",
                    "Effect": "Deny",
                    "Action": "s3:*",
                    "Resource": "arn:aws:s3:::vault-bucket/public/*"
                },
                {
                    "Sid": "KmsForVault",
                    "Effect": "Allow",
                    "Action": "kms:*",
                    "Resource": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48"
                }
            ]
        },
        "VersionId": "v1",
        "IsDefaultVersion": true,
        "CreateDate": "2026-05-17T07:48:44.526422+00:00"
    }
}

[stdout]
{
    "PolicyVersion": {
        "Document": {
            "Version": "2012-10-17",
            "Statement": [
                {
                    "Sid": "BucketListing",
                    "Effect": "Allow",
                    "Action": [
                        "s3:ListBucket",
                        "s3:GetBucketLocation"
                    ],
                    "NotResource": "arn:aws:s3:::vault-bucket/public/*"
                },
                {
                    "Sid": "ObjectOps",
                    "Effect": "Allow",
                    "Action": [
                        "s3:GetObject",
                        "s3:PutObject",
                        "s3:DeleteObject"
                    ],
                    "Resource": "arn:aws:s3:::vault-bucket/Confidential/*"
                },
                {
                    "Sid": "PublicGuard",
                    "Effect": "Deny",
                    "Action": "s3:*",
                    "Resource": "arn:aws:s3:::vault-bucket/public/*"
                },
                {
                    "Sid": "KmsForVault",
                    "Effect": "Allow",
                    "Action": "kms:*",
                    "Resource": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48"
                }
            ]
        },
        "VersionId": "v1",
        "IsDefaultVersion": true,
        "CreateDate": "2026-05-17T07:48:44.526422+00:00"
    }
}

Bash

{
  "command": "aws iam get-policy-version --policy-arn arn:aws:iam::000000000000:policy/AnalystIdentityPolicy --version-id v1 --region us-east-1 --output json",
  "description": "Get AnalystIdentityPolicy v1"
}

output

{
    "PolicyVersion": {
        "Document": {
            "Version": "2012-10-17",
            "Statement": [
                {
                    "Sid": "AnalystS3",
                    "Effect": "Allow",
                    "Action": "s3:*",
                    "Resource": "*"
                },
                {
                    "Sid": "AnalystKms",
                    "Effect": "Allow",
                    "Action": "kms:*",
                    "Resource": "*"
                },
                {
                    "Sid": "AnalystGuard",
                    "Effect": "Deny",
                    "Action": "s3:PutObject",
                    "Resource": "arn:aws:s3:::vault-bucket/public/*"
                }
            ]
        },
        "VersionId": "v1",
        "IsDefaultVersion": true,
        "CreateDate": "2026-05-17T07:48:44.179109+00:00"
    }
}

[stdout]
{
    "PolicyVersion": {
        "Document": {
            "Version": "2012-10-17",
            "Statement": [
                {
                    "Sid": "AnalystS3",
                    "Effect": "Allow",
                    "Action": "s3:*",
                    "Resource": "*"
                },
                {
                    "Sid": "AnalystKms",
                    "Effect": "Allow",
                    "Action": "kms:*",
                    "Resource": "*"
                },
                {
                    "Sid": "AnalystGuard",
                    "Effect": "Deny",
                    "Action": "s3:PutObject",
                    "Resource": "arn:aws:s3:::vault-bucket/public/*"
                }
            ]
        },
        "VersionId": "v1",
        "IsDefaultVersion": true,
        "CreateDate": "2026-05-17T07:48:44.179109+00:00"
    }
}

Bash

{
  "command": "aws iam list-attached-user-policies --user-name analyst-user --region us-east-1 --output json",
  "description": "List user policies"
}

output

{
    "AttachedPolicies": [
        {
            "PolicyName": "AnalystIdentityPolicy",
            "PolicyArn": "arn:aws:iam::000000000000:policy/AnalystIdentityPolicy"
        }
    ]
}

[stdout]
{
    "AttachedPolicies": [
        {
            "PolicyName": "AnalystIdentityPolicy",
            "PolicyArn": "arn:aws:iam::000000000000:policy/AnalystIdentityPolicy"
        }
    ]
}

Bash

{
  "command": "aws iam list-policy-versions --policy-arn arn:aws:iam::000000000000:policy/AnalystBoundary --region us-east-1 --output json; aws iam list-policy-versions --policy-arn arn:aws:iam::000000000000:policy/AnalystIdentityPolicy --region us-east-1 --output json",
  "description": "List policy versions"
}

output

{
    "Versions": [
        {
            "VersionId": "v2",
            "IsDefaultVersion": false,
            "CreateDate": "2026-05-17T07:48:44.884667+00:00"
        },
        {
            "VersionId": "v1",
            "IsDefaultVersion": true,
            "CreateDate": "2026-05-17T07:48:44.526422+00:00"
        }
    ]
}
{
    "Versions": [
        {
            "VersionId": "v1",
            "IsDefaultVersion": true,
            "CreateDate": "2026-05-17T07:48:44.179109+00:00"
        }
    ]
}

[stdout]
{
    "Versions": [
        {
            "VersionId": "v2",
            "IsDefaultVersion": false,
            "CreateDate": "2026-05-17T07:48:44.884667+00:00"
        },
        {
            "VersionId": "v1",
            "IsDefaultVersion": true,
            "CreateDate": "2026-05-17T07:48:44.526422+00:00"
        }
    ]
}
{
    "Versions": [
        {
            "VersionId": "v1",
            "IsDefaultVersion": true,
            "CreateDate": "2026-05-17T07:48:44.179109+00:00"
        }
    ]
}

Bash

{
  "command": "aws iam get-policy-version --policy-arn arn:aws:iam::000000000000:policy/AnalystBoundary --version-id v2 --region us-east-1 --output json",
  "description": "Check v2 of boundary"
}

output

{
    "PolicyVersion": {
        "Document": {
            "Version": "2012-10-17",
            "Statement": [
                {
                    "Sid": "BucketListing",
                    "Effect": "Allow",
                    "Action": [
                        "s3:ListBucket",
                        "s3:GetBucketLocation"
                    ],
                    "Resource": "arn:aws:s3:::vault-bucket",
                    "Condition": {
                        "StringLike": {
                            "s3:prefix": [
                                "confidential/*"
                            ]
                        }
                    }
                },
                {
                    "Sid": "ObjectOps",
                    "Effect": "Allow",
                    "Action": [
                        "s3:GetObject",
                        "s3:PutObject",
                        "s3:DeleteObject"
                    ],
                    "Resource": "arn:aws:s3:::vault-bucket/confidential/*"
                },
                {
                    "Sid": "KmsForVault",
                    "Effect": "Allow",
                    "Action": [
                        "kms:Encrypt",
                        "kms:Decrypt",
                        "kms:GenerateDataKey",
                        "kms:GenerateDataKeyWithoutPlaintext",
                        "kms:DescribeKey"
                    ],
                    "Resource": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48"
                }
            ]
        },
        "VersionId": "v2",
        "IsDefaultVersion": false,
        "CreateDate": "2026-05-17T07:48:44.884667+00:00"
    }
}

[stdout]
{
    "PolicyVersion": {
        "Document": {
            "Version": "2012-10-17",
            "Statement": [
                {
                    "Sid": "BucketListing",
                    "Effect": "Allow",
                    "Action": [
                        "s3:ListBucket",
                        "s3:GetBucketLocation"
                    ],
                    "Resource": "arn:aws:s3:::vault-bucket",
                    "Condition": {
                        "StringLike": {
                            "s3:prefix": [
                                "confidential/*"
                            ]
                        }
                    }
                },
                {
                    "Sid": "ObjectOps",
                    "Effect": "Allow",
                    "Action": [
                        "s3:GetObject",
                        "s3:PutObject",
                        "s3:DeleteObject"
                    ],
                    "Resource": "arn:aws:s3:::vault-bucket/confidential/*"
                },
                {
                    "Sid": "KmsForVault",
                    "Effect": "Allow",
                    "Action": [
                        "kms:Encrypt",
                        "kms:Decrypt",
                        "kms:GenerateDataKey",
                        "kms:GenerateDataKeyWithoutPlaintext",
                        "kms:DescribeKey"
                    ],
                    "Resource": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48"
                }
            ]
        },
        "VersionId": "v2",
        "IsDefaultVersion": false,
        "CreateDate": "2026-05-17T07:48:44.884667+00:00"
    }
}

Bash

{
  "command": "aws s3api list-buckets --region us-east-1 --output json; aws kms list-aliases --region us-east-1 --output json | head -40; aws iam list-access-keys --user-name analyst-user --region us-east-1 --output json",
  "description": "Check bucket, kms, access keys"
}

output

{
    "Buckets": [
        {
            "Name": "vault-bucket",
            "CreationDate": "2026-05-17T07:48:42+00:00",
            "BucketRegion": "us-east-1",
            "BucketArn": "arn:aws:s3:::vault-bucket"
        }
    ],
    "Owner": {
        "ID": "75aa57f09aa0c8caeab4f8c24e99d10f8e7faeebf76c078efc7c6caea54ba06a"
    },
    "Prefix": null
}
{
    "Aliases": [
        {
            "AliasName": "alias/vault-kms",
            "AliasArn": "arn:aws:kms:us-east-1:000000000000:alias/vault-kms",
            "TargetKeyId": "4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48",
            "CreationDate": "2026-05-17T07:48:41.763833+00:00"
        }
    ]
}
{
    "AccessKeyMetadata": [
        {
            "UserName": "analyst-user",
            "AccessKeyId": "LKIAQAAAAAAANHRXNXRG",
            "Status": "Active",
            "CreateDate": "2026-05-17T07:48:46.066116+00:00"
        }
    ]
}

[stdout]
{
    "Buckets": [
        {
            "Name": "vault-bucket",
            "CreationDate": "2026-05-17T07:48:42+00:00",
            "BucketRegion": "us-east-1",
            "BucketArn": "arn:aws:s3:::vault-bucket"
        }
    ],
    "Owner": {
        "ID": "75aa57f09aa0c8caeab4f8c24e99d10f8e7faeebf76c078efc7c6caea54ba06a"
    },
    "Prefix": null
}
{
    "Aliases": [
        {
            "AliasName": "alias/vault-kms",
            "AliasArn": "arn:aws:kms:us-east-1:000000000000:alias/vault-kms",
            "TargetKeyId": "4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48",
            "CreationDate": "2026-05-17T07:48:41.763833+00:00"
        }
    ]
}
{
    "AccessKeyMetadata": [
        {
            "UserName": "analyst-user",
            "AccessKeyId": "LKIAQAAAAAAANHRXNXRG",
            "Status": "Active",
            "CreateDate": "2026-05-17T07:48:46.066116+00:00"
        }
    ]
}

Diagnosis confirmed. Issues found: 1. **Identity policy gates** , it contains a `Deny s3:PutObject` on `public/*`. Spec says identity must stay broad (`s3:*`/`kms:*` on `*`) so the boundary ∩ identity intersection is observable. 2. **Boundary's default version (v1) is wrong** , uses `Confidential/*` (wrong case), has a `NotResource` ListBucket and explicit Deny; the existing v2 is correctly shaped (only the ceiling, lowercase, proper KMS list). Need to promote v2 to default. 3. **`analyst-user` has no `PermissionsBoundary` attached** , the auditor's required signal is missing. 4. **SSM `/harbor/boundary/policy-arn`** points at `policy/AnalystBoundaryPolicy` but the actual (and spec-required) name is `AnalystBoundary`. Update the pointer. Fixing in place , promote boundary v2, replace identity doc with a non-gating version, attach the boundary to the user, and fix the SSM pointer.

Bash

{
  "command": "aws iam set-default-policy-version --policy-arn arn:aws:iam::000000000000:policy/AnalystBoundary --version-id v2 --region us-east-1 && echo \"Set boundary v2 as default\"",
  "description": "Promote boundary v2 to default"
}

output

Set boundary v2 as default

[stdout]
Set boundary v2 as default

Bash

{
  "command": "aws iam put-user-permissions-boundary --user-name analyst-user --permissions-boundary arn:aws:iam::000000000000:policy/AnalystBoundary --region us-east-1 && echo \"Boundary attached to user\"",
  "description": "Attach boundary to analyst-user"
}

output

Boundary attached to user

[stdout]
Boundary attached to user

Bash

{
  "command": "aws ssm put-parameter --name /harbor/boundary/policy-arn --type String --value arn:aws:iam::000000000000:policy/AnalystBoundary --overwrite --region us-east-1 && echo \"SSM pointer fixed\"",
  "description": "Fix SSM policy-arn pointer"
}

output

{
    "Version": 2,
    "Tier": "Standard"
}
SSM pointer fixed

[stdout]
{
    "Version": 2,
    "Tier": "Standard"
}
SSM pointer fixed

Now replace the identity policy document to drop its gating Deny , keep it broad.

Write

{
  "file_path": "/tmp/identity.json",
  "content": "{\n  \"Version\": \"2012-10-17\",\n  \"Statement\": [\n    {\n      \"Sid\": \"AnalystS3\",\n      \"Effect\": \"Allow\",\n      \"Action\": \"s3:*\",\n      \"Resource\": \"*\"\n    },\n    {\n      \"Sid\": \"AnalystKms\",\n      \"Effect\": \"Allow\",\n      \"Action\": \"kms:*\",\n      \"Resource\": \"*\"\n    }\n  ]\n}\n"
}

output

File created successfully at: /tmp/identity.json (file state is current in your context , no need to Read it back)

Bash

{
  "command": "aws iam create-policy-version --policy-arn arn:aws:iam::000000000000:policy/AnalystIdentityPolicy --policy-document file:///tmp/identity.json --set-as-default --region us-east-1 --output json",
  "description": "Create new identity policy version"
}

output

{
    "PolicyVersion": {
        "VersionId": "v2",
        "IsDefaultVersion": true,
        "CreateDate": "2026-05-17T07:53:45.449625+00:00"
    }
}

[stdout]
{
    "PolicyVersion": {
        "VersionId": "v2",
        "IsDefaultVersion": true,
        "CreateDate": "2026-05-17T07:53:45.449625+00:00"
    }
}

Now verify the wiring end-to-end against the required behaviour.

Bash

{
  "command": "aws iam get-user --user-name analyst-user --region us-east-1 --output json",
  "description": "Verify PermissionsBoundary on user"
}

output

{
    "User": {
        "Path": "/",
        "UserName": "analyst-user",
        "UserId": "AIDAQAAAAAAACIBMMHTQF",
        "Arn": "arn:aws:iam::000000000000:user/analyst-user",
        "CreateDate": "2026-05-17T07:48:45.276665+00:00",
        "PermissionsBoundary": {
            "PermissionsBoundaryType": "Policy",
            "PermissionsBoundaryArn": "arn:aws:iam::000000000000:policy/AnalystBoundary"
        }
    }
}

[stdout]
{
    "User": {
        "Path": "/",
        "UserName": "analyst-user",
        "UserId": "AIDAQAAAAAAACIBMMHTQF",
        "Arn": "arn:aws:iam::000000000000:user/analyst-user",
        "CreateDate": "2026-05-17T07:48:45.276665+00:00",
        "PermissionsBoundary": {
            "PermissionsBoundaryType": "Policy",
            "PermissionsBoundaryArn": "arn:aws:iam::000000000000:policy/AnalystBoundary"
        }
    }
}

Bash

{
  "command": "aws iam get-policy-version --policy-arn arn:aws:iam::000000000000:policy/AnalystBoundary --version-id v2 --region us-east-1 --query 'PolicyVersion.IsDefaultVersion'; aws iam get-policy-version --policy-arn arn:aws:iam::000000000000:policy/AnalystIdentityPolicy --version-id v2 --region us-east-1 --query 'PolicyVersion.IsDefaultVersion'",
  "description": "Verify defaults"
}

output

true
true

[stdout]
true
true

Boundary attached, defaults correct. Now the behavioural test, signing with the analyst's keys under `ENFORCE_IAM=1`.

Bash

{
  "command": "export AK=$(aws ssm get-parameter --name /harbor/boundary/analyst-access-key-id --region us-east-1 --query Parameter.Value --output text)\nexport SK=$(aws ssm get-parameter --name /harbor/boundary/analyst-secret-key --with-decryption --region us-east-1 --query Parameter.Value --output text)\necho \"AK=$AK len(SK)=${#SK}\"",
  "description": "Load analyst credentials from SSM"
}

output

AK=LKIAQAAAAAAANHRXNXRG len(SK)=40

[stdout]
AK=LKIAQAAAAAAANHRXNXRG len(SK)=40

Bash

{
  "command": "set +e\nAK=$(aws ssm get-parameter --name /harbor/boundary/analyst-access-key-id --region us-east-1 --query Parameter.Value --output text)\nSK=$(aws ssm get-parameter --name /harbor/boundary/analyst-secret-key --with-decryption --region us-east-1 --query Parameter.Value --output text)\nKMS_ARN=$(aws ssm get-parameter --name /harbor/boundary/kms-key-arn --region us-east-1 --query Parameter.Value --output text)\nKMS_KEY_ID=${KMS_ARN##*/}\n\nrun() { echo \"=== $1 ===\"; shift; AWS_ACCESS_KEY_ID=$AK AWS_SECRET_ACCESS_KEY=$SK ENFORCE_IAM=1 AWS_REGION=us-east-1 \"$@\" 2>&1 | tail -20; echo; }\n\necho hello > /tmp/cf.txt\necho hello > /tmp/pub.txt\n\nrun \"PutObject confidential (should ALLOW)\" aws s3api put-object --bucket vault-bucket --key confidential/test1.txt --body /tmp/cf.txt --server-side-encryption aws:kms --ssekms-key-id \"$KMS_ARN\"\nrun \"GetObject confidential (should ALLOW)\" aws s3api get-object --bucket vault-bucket --key confidential/test1.txt /tmp/out.txt\nrun \"PutObject public (should DENY)\" aws s3api put-object --bucket vault-bucket --key public/test.txt --body /tmp/pub.txt\nrun \"PutObject other bucket (should DENY)\" aws s3api put-object --bucket some-other-bucket --key x.txt --body /tmp/pub.txt\nrun \"kms:CreateKey (should DENY)\" aws kms create-key --description \"shouldnt\"\nrun \"kms:GenerateDataKey on vault cmk (should ALLOW)\" aws kms generate-data-key --key-id \"$KMS_ARN\" --key-spec AES_256\nrun \"kms:Decrypt path: encrypt with vault cmk first\" aws kms encrypt --key-id \"$KMS_ARN\" --plaintext \"$(echo hello | base64)\"",
  "description": "End-to-end behaviour tests as analyst"
}

output

=== PutObject confidential (should ALLOW) ===
{
    "ETag": "\"b1946ac92492d2347c6235b4d2611184\"",
    "ChecksumCRC64NVME": "akP7S61aVgc=",
    "ChecksumType": "FULL_OBJECT",
    "ServerSideEncryption": "aws:kms",
    "SSEKMSKeyId": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48",
    "BucketKeyEnabled": true
}

=== GetObject confidential (should ALLOW) ===
{
    "AcceptRanges": "bytes",
    "LastModified": "2026-05-17T07:54:16+00:00",
    "ContentLength": 6,
    "ETag": "\"b1946ac92492d2347c6235b4d2611184\"",
    "ChecksumCRC64NVME": "akP7S61aVgc=",
    "ChecksumType": "FULL_OBJECT",
    "ContentType": "binary/octet-stream",
    "ServerSideEncryption": "aws:kms",
    "Metadata": {},
    "SSEKMSKeyId": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48",
    "BucketKeyEnabled": true
}

=== PutObject public (should DENY) ===

aws: [ERROR]: An error occurred (AccessDenied) when calling the PutObject operation: Access Denied

=== PutObject other bucket (should DENY) ===

aws: [ERROR]: An error occurred (AccessDenied) when calling the PutObject operation: Access Denied

=== kms:CreateKey (should DENY) ===

aws: [ERROR]: An error occurred (AccessDeniedException) when calling the CreateKey operation: User: arn:aws:iam::000000000000:user/analyst-user is not authorized to perform: kms:CreateKey on resource: * because no identity-based policy allows the kms:CreateKey action

=== kms:GenerateDataKey on vault cmk (should ALLOW) ===
{
    "CiphertextBlob": "NGJkNGQyZGQtZGY2MC00ZDU2LTgzMmMtYjZlN2E0ZTNhZTQ4SLeCwNG+xXBlpPLa+TMODbzlsPHMw0ImZPyvkupmgItU6FgfeDnYk/m3nZgAWkUvGthSTaliP9AudWM2u7Zg8k14nMA0GZn/s/dB1wNeOHI=",
    "Plaintext": "eBu1aE4L2qLAosxV5Olc0NyRXDhsBdcxKWuYOZtl1Io=",
    "KeyId": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48"
}

=== kms:Decrypt path: encrypt with vault cmk first ===
{
    "CiphertextBlob": "NGJkNGQyZGQtZGY2MC00ZDU2LTgzMmMtYjZlN2E0ZTNhZTQ4lhOiDJS+afYrS1dNEUOPI1iXqmX4uaE3jLx8jeg0JQ09nLc0BRKBPFc3TbVOeAUl",
    "KeyId": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48"
}

[stdout]
=== PutObject confidential (should ALLOW) ===
{
    "ETag": "\"b1946ac92492d2347c6235b4d2611184\"",
    "ChecksumCRC64NVME": "akP7S61aVgc=",
    "ChecksumType": "FULL_OBJECT",
    "ServerSideEncryption": "aws:kms",
    "SSEKMSKeyId": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48",
    "BucketKeyEnabled": true
}

=== GetObject confidential (should ALLOW) ===
{
    "AcceptRanges": "bytes",
    "LastModified": "2026-05-17T07:54:16+00:00",
    "ContentLength": 6,
    "ETag": "\"b1946ac92492d2347c6235b4d2611184\"",
    "ChecksumCRC64NVME": "akP7S61aVgc=",
    "ChecksumType": "FULL_OBJECT",
    "ContentType": "binary/octet-stream",
    "ServerSideEncryption": "aws:kms",
    "Metadata": {},
    "SSEKMSKeyId": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48",
    "BucketKeyEnabled": true
}

=== PutObject public (should DENY) ===

aws: [ERROR]: An error occurred (AccessDenied) when calling the PutObject operation: Access Denied

=== PutObject other bucket (should DENY) ===

aws: [ERROR]: An error occurred (AccessDenied) when calling the PutObject operation: Access Denied

=== kms:CreateKey (should DENY) ===

aws: [ERROR]: An error occurred (AccessDeniedException) when calling the CreateKey operation: User: arn:aws:iam::000000000000:user/analyst-user is not authorized to perform: kms:CreateKey on resource: * because no identity-based policy allows the kms:CreateKey action

=== kms:GenerateDataKey on vault cmk (should ALLOW) ===
{
    "CiphertextBlob": "NGJkNGQyZGQtZGY2MC00ZDU2LTgzMmMtYjZlN2E0ZTNhZTQ4SLeCwNG+xXBlpPLa+TMODbzlsPHMw0ImZPyvkupmgItU6FgfeDnYk/m3nZgAWkUvGthSTaliP9AudWM2u7Zg8k14nMA0GZn/s/dB1wNeOHI=",
    "Plaintext": "eBu1aE4L2qLAosxV5Olc0NyRXDhsBdcxKWuYOZtl1Io=",
    "KeyId": "arn:aws:kms:us-east-1:000000000000:key/4bd4d2dd-df60-4d56-832c-b6e7a4e3ae48"
}

=== kms:Decr
…[truncated]

All five required behaviours pass end-to-end signed with the analyst's keys under `ENFORCE_IAM=1`: | check | result | |-|-| | `PutObject`/`GetObject` on `vault-bucket/confidential/*` | allow ✓ | | `PutObject` on `vault-bucket/public/*` | `AccessDenied` ✓ | | `PutObject` on a different bucket | `AccessDenied` ✓ | | `kms:CreateKey` | `AccessDeniedException` ✓ | | `kms:GenerateDataKey` / `kms:Decrypt` on the vault cmk | allow ✓ | And the auditor signal: `iam:GetUser analyst-user` returns `PermissionsBoundary.PermissionsBoundaryArn = arn:aws:iam::000000000000:policy/AnalystBoundary`. What was wrong, and the in-place fixes: - `AnalystBoundary` default version was `v1` (had `Confidential` mis-case, a `NotResource` ListBucket, and an explicit Deny). A correctly-shaped `v2` already existed. Promoted `v2` to default via `set-default-policy-version` , no recreate needed. - `analyst-user` had no permissions boundary. Attached it in place with `put-user-permissions-boundary`. - `AnalystIdentityPolicy` carried a `Deny s3:PutObject` on `public/*` , gating in the identity policy defeats the whole point. Replaced with a new default version that's just `s3:* on *` and `kms:* on *`. - SSM `/harbor/boundary/policy-arn` pointed at the wrong name (`AnalystBoundaryPolicy`). Repointed to the real arn `…:policy/AnalystBoundary`.

Final diff , what the agent changed

No file changes, the agent left the workspace untouched.

Verifier output , the proof behind the reward

tests/test.sh

downloading uv 0.9.7 aarch64-unknown-linux-gnu
Downloading botocore (12.7MiB)
Downloading pygments (1.2MiB)
 Downloading pygments
 Downloading botocore
Installed 13 packages in 27ms
============================= test session starts ==============================
platform linux -- Python 3.12.3, pytest-8.4.1, pluggy-1.6.0 -- /root/.cache/uv/archive-v0/2xPRADEQjrtaY0z4tRFkt/bin/python
cachedir: .pytest_cache
rootdir: /tests
plugins: json-ctrf-0.3.5
collecting ... collected 27 items

../tests/test_outputs.py::test_01_analyst_user_exists PASSED             [  3%]
../tests/test_outputs.py::test_02_identity_policy_attached_to_user PASSED [  7%]
../tests/test_outputs.py::test_03_boundary_attached_via_get_user PASSED  [ 11%]
../tests/test_outputs.py::test_04_vault_bucket_exists_with_public_access_block PASSED [ 14%]
../tests/test_outputs.py::test_05_kms_alias_and_ssm_pointers_resolve PASSED [ 18%]
../tests/test_outputs.py::test_06_identity_policy_grants_full_s3_and_full_kms PASSED [ 22%]
../tests/test_outputs.py::test_07_identity_policy_has_no_explicit_deny_anywhere PASSED [ 25%]
../tests/test_outputs.py::test_08_user_has_no_admin_managed_policy_attached PASSED [ 29%]
../tests/test_outputs.py::test_09_boundary_effect_allow_only PASSED      [ 33%]
../tests/test_outputs.py::test_10_boundary_has_no_NotResource_or_NotAction PASSED [ 37%]
../tests/test_outputs.py::test_11_boundary_object_actions_scoped_to_confidential_prefix PASSED [ 40%]
../tests/test_outputs.py::test_12_boundary_listbucket_uses_s3_prefix_condition PASSED [ 44%]
../tests/test_outputs.py::test_13_boundary_kms_actions_scoped_to_cmk_arn PASSED [ 48%]
../tests/test_outputs.py::test_14_boundary_does_not_grant_kms_create_key_or_wildcard_kms PASSED [ 51%]
../tests/test_outputs.py::test_15_boundary_does_not_grant_iam_self_modify PASSED [ 55%]
../tests/test_outputs.py::test_16_boundary_size_under_managed_policy_limit PASSED [ 59%]
../tests/test_outputs.py::test_17_boundary_allows_confidential_put_via_simulator PASSED [ 62%]
../tests/test_outputs.py::test_18_boundary_denies_public_put_via_simulator PASSED [ 66%]
../tests/test_outputs.py::test_19_boundary_allows_kms_decrypt_via_simulator PASSED [ 70%]
../tests/test_outputs.py::test_20_boundary_denies_kms_create_key_via_simulator PASSED [ 74%]
../tests/test_outputs.py::test_21_analyst_can_put_to_confidential_prefix PASSED [ 77%]
../tests/test_outputs.py::test_22_analyst_cannot_put_to_public_prefix PASSED [ 81%]
../tests/test_outputs.py::test_23_analyst_cannot_create_kms_key PASSED   [ 85%]
../tests/test_outputs.py::test_24_analyst_cannot_put_to_a_different_bucket PASSED [ 88%]
../tests/test_outputs.py::test_25_boundary_object_resource_prefix_is_lowercase_confidential PASSED [ 92%]
../tests/test_outputs.py::test_26_ssm_policy_arn_resolves_to_a_live_boundary_managed_policy PASSED [ 96%]
../tests/test_outputs.py::test_27_boundary_default_version_reflects_the_runtime_intended_shape PASSED [100%]

=============================== warnings summary ===============================
test_outputs.py: 54 warnings
  /root/.cache/uv/archive-v0/2xPRADEQjrtaY0z4tRFkt/lib/python3.12/site-packages/botocore/auth.py:424: DeprecationWarning: datetime.datetime.utcnow() is deprecated and scheduled for removal in a future version. Use timezone-aware objects to represent datetimes in UTC: datetime.datetime.now(datetime.UTC).
    datetime_now = datetime.datetime.utcnow()

-- Docs: https://docs.pytest.org/en/stable/how-to/capture-warnings.html
==================================== PASSES ====================================
=========================== short test summary info ============================
PASSED ../tests/test_outputs.py::test_01_analyst_user_exists
PASSED ../tests/test_outputs.py::test_02_identity_policy_attached_to_user
PASSED ../tests/test_outputs.py::test_03_boundary_attached_via_get_user
PASSED ../tests/test_outputs.py::test_04_vault_bucket_exists_with_public_access_block
PASSED ../tests/test_outputs.py::test_05_kms_alias_and_ssm_pointers_resolve
PASSED ../tests/test_outputs.py::test_06_identity_policy_grants_full_s3_and_full_kms
PASSED ../tests/test_outputs.py::test_07_identity_policy_has_no_explicit_deny_anywhere
PASSED ../tests/test_outputs.py::test_08_user_has_no_admin_managed_policy_attached
PASSED ../tests/test_outputs.py::test_09_boundary_effect_allow_only
PASSED ../tests/test_outputs.py::test_10_boundary_has_no_NotResource_or_NotAction
PASSED ../tests/test_outputs.py::test_11_boundary_object_actions_scoped_to_confidential_prefix
PASSED ../tests/test_outputs.py::test_12_boundary_listbucket_uses_s3_prefix_condition
PASSED ../tests/test_outputs.py::test_13_boundary_kms_actions_scoped_to_cmk_arn
PASSED ../tests/test_outputs.py::test_14_boundary_does_not_grant_kms_create_key_or_wildcard_kms
PASSED ../tests/test_outputs.py::test_15_boundary_does_not_grant_iam_self_modify
PASSED ../tests/test_outputs.py::test_16_boundary_size_under_managed_policy_limit
PASSED ../tests/test_outputs.py::test_17_boundary_allows_confidential_put_via_simulator
PASSED ../tests/test_outputs.py::test_18_boundary_denies_public_put_via_simulator
PASSED ../tests/test_outputs.py::test_19_boundary_allows_kms_decrypt_via_simulator
PASSED ../tests/test_outputs.py::test_20_boundary_denies_kms_create_key_via_simulator
PASSED ../tests/test_outputs.py::test_21_analyst_can_put_to_confidential_prefix
PASSED ../tests/test_outputs.py::test_22_analyst_cannot_put_to_public_prefix
PASSED ../tests/test_outputs.py::test_23_analyst_cannot_create_kms_key
PASSED ../tests/test_outputs.py::test_24_analyst_cannot_put_to_a_different_bucket
PASSED ../tests/test_outputs.py::test_25_boundary_object_resource_prefix_is_lowercase_confidential
PASSED ../tests/test_outputs.py::test_26_ssm_policy_arn_resolves_to_a_live_boundary_managed_policy
PASSED ../tests/test_outputs.py::test_27_boundary_default_version_reflects_the_runtime_intended_shape
======================= 27 passed, 54 warnings in 0.57s ========================

Reproduce this trial: git checkout 2f94510 && PYTHONPATH=src python3 scripts/build_site.py , then open trial/trial_ac2e4bca60f44f1b. Re-running the agent live requires EVAL_PLATFORM_ENABLE_OAUTH_SMOKE=1 and is non-deterministic.

Trial trial_ac2e4bca60f44f1b · verifier authoritative; classifier explanatory.