Connecting On Premises Networks

Domain expertise for the transit gateway side of reaching on-premises data centers through one hub, over a Site-to-Site VPN or AWS Direct Connect, instead of a separate tunnel into each VPC. Covers the static-versus-dynamic VPN routing difference, equal-cost multi-path (ECMP) across multiple tunnels and what it requires, the accelerated Site-to-Site VPN option, and the association and propagation wiring that decides where on-premises routes land.

Does not cover the Direct Connect gateway and virtual interface setup, which belongs to the directconnect skill. This reference covers the transit-gateway-side configuration only. Creating the hub, segmentation, egress, peering, and multicast are separate references.

Execute commands using the AWS MCP server when connected (sandboxed execution, audit logging, observability). Fall back to the AWS CLI otherwise. A transit gateway is Regional; run every command in the Region that holds the hub.

Table of Contents

• Overview
• Workflow
• Decision: static vs dynamic VPN routing
• ECMP across multiple tunnels
• Accelerated Site-to-Site VPN
• Association and propagation wiring
• Direct Connect side belongs to the directconnect skill
• Security considerations
• Troubleshooting
• Procedure
• Additional Resources

Workflow

To connect on-premises over the transit gateway end to end, follow the procedure exactly. See the Procedure section below. It covers creating the VPN attachment (or, for Direct Connect, associating the Direct Connect gateway after the directconnect skill has set it up), choosing the routing model, deciding on ECMP and accelerated VPN, wiring association and propagation, and surfacing the console link to verify.

Decision: static vs dynamic VPN routing

Constraints:

• You MUST call out that static routes targeting a VPN attachment are not filtered, when the customer picks static
• You MUST add the static routes to the transit gateway route table as a required step when static is chosen
• You SHOULD prefer dynamic (BGP) routing where the customer gateway device supports it

ECMP across multiple tunnels

Customers attach multiple Site-to-Site VPN tunnels to aggregate bandwidth and expect the traffic to spread, then find it pins to one tunnel. Equal-cost multi-path (ECMP) routing is only supported with dynamic (BGP) routing, not static, and only when the tunnels terminate on the same transit gateway.

Constraints:

• You MUST confirm BGP is in use before promising bandwidth aggregation across tunnels
• You MUST confirm the tunnels terminate on the same transit gateway for ECMP to apply
• You MUST NOT promise aggregation for static tunnels, since they will not spread load

Accelerated Site-to-Site VPN

When a customer chooses VPN over Direct Connect for cost or simplicity, the accelerated Site-to-Site VPN option routes the tunnel over the AWS global network through Global Accelerator edge locations and materially improves latency and jitter. It is set at VPN creation and is not discoverable in the standard flow.

Constraints:

• You SHOULD surface accelerated VPN as a decision point when the customer chooses VPN, so they can weigh the performance gain before the connection is built
• You MUST set the accelerated option at VPN creation, since it cannot be toggled on an existing VPN

Association and propagation wiring

After the attachment, on-premises prefixes only reach the VPCs whose attachments share a route table with the path. Finishing the attachment does not make on-premises routes appear everywhere.

Constraints:

• You MUST confirm the association and propagation wiring so the hybrid routes land where the customer expects
• You MUST verify the on-premises prefixes reach the intended VPC attachments, not assume they propagate everywhere

Direct Connect side belongs to the directconnect skill

Associating a Direct Connect gateway with the transit gateway, assigning a unique Autonomous System Number per transit gateway, and checking the Direct Connect gateway is free of conflicting virtual private gateway or private virtual interface bindings are Direct Connect concerns.

Constraints:

• You MUST route the Direct Connect gateway and virtual interface setup to the directconnect skill, specifically the “connecting many VPCs through a Direct Connect gateway” reference
• You MUST NOT restate the Direct Connect side here; cover only the transit gateway association once the Direct Connect gateway exists

Security considerations

Hybrid connectivity extends the trust boundary to an on-premises network over a tunnel that carries sensitive traffic and connection state, so encryption, credential handling, and route hygiene matter here. The controls are embedded in the procedure; this section consolidates them.

Constraints:

• You MUST set Site-to-Site VPN tunnel options that enforce strong encryption (IKEv2 with AES-256 and AES256-GCM-16) rather than relying on AWS defaults, which may permit weaker ciphers
• You MUST, when a customer-specified pre-shared key (PSK) is used (via TunnelOptions[].PreSharedKey), store and retrieve it from AWS Secrets Manager, never hardcoding it in scripts or configuration files; prefer the AWS-generated PSK when no specific value is required
• You MUST call out that static routes targeting a VPN attachment are not filtered and can allow unintended outbound traffic, and SHOULD prefer dynamic (BGP) routing where the customer gateway device supports it
• You SHOULD enable Site-to-Site VPN tunnel logging to CloudWatch Logs with encryption enabled, since the logs carry connection state and IKE negotiation detail
• You MUST enable VPC Flow Logs on the attached VPC subnets and Transit Gateway Flow Logs on the hub with encryption at rest on the destination, and you SHOULD enable AWS CloudTrail (encrypted) to detect unauthorized changes to attachments, route tables, associations, and propagations
• You MUST, when a KMS key encrypts a flow log, tunnel log, or CloudTrail destination, scope the KMS key policy with condition keys (aws:SourceArn, aws:SourceAccount, kms:ViaService) so only the specific log group, bucket, or trail in the expected account and service can use the key
• You SHOULD apply least-privilege IAM for transit gateway administration, avoiding service wildcards and FullAccess policies

Troubleshooting

Unintended outbound traffic over a static VPN

Static routes to a VPN attachment are not filtered. Tighten the routes or move to dynamic (BGP).

Multiple VPN tunnels do not aggregate bandwidth

ECMP needs BGP and tunnels on the same transit gateway. Confirm both; static will not aggregate.

VPN performance is poor over the public internet

The accelerated VPN option was not chosen. It must be set at creation; recreate the VPN to enable it.

On-premises routes do not reach a VPC

The attachment does not share a route table with the path. Fix the association and propagation.

Procedure

Overview

This procedure creates the VPN attachment with the right routing model, decides ECMP and accelerated VPN, wires association and propagation, and surfaces the console link to verify. For Direct Connect, it assumes the directconnect skill has set up the Direct Connect gateway.

Parameters

• region (required): The Region that holds the hub.
• transit_gateway_id (required): The transit gateway.
• connection_type (required): vpn or directconnect.
• vpn_routing (required for VPN): dynamic or static.
• customer_gateway_id (required for VPN): The customer gateway device.
• accelerated (optional for VPN): Whether to use the accelerated VPN option.
• dx_gateway_id (required for Direct Connect): The Direct Connect gateway ID created by the directconnect skill.
• allowed_prefix (required for Direct Connect): The CIDR prefix to allow through the Direct Connect gateway association.

Constraints for parameter acquisition:

• You MUST ask for all required parameters upfront in a single prompt
• You MUST ask whether bandwidth aggregation across tunnels is needed (decides BGP and ECMP)

Steps

1. Verify dependencies

Constraints:

• You MUST confirm credentials with aws sts get-caller-identity, and you MUST use short-lived, ephemeral credentials scoped to least privilege for transit gateway administration, never long-lived access keys or broad service wildcard or FullAccess policies
• You MUST, for Direct Connect, confirm the directconnect skill has created the Direct Connect gateway before associating it
• You MUST enable VPC Flow Logs on the attached VPC subnets and Transit Gateway Flow Logs on the hub for traffic visibility, audit, and incident response across every attached network. These logs carry sensitive traffic data, so you MUST enable encryption at rest on the destination (a KMS key on the CloudWatch log group, or SSE-KMS on the S3 bucket)
• You SHOULD enable AWS CloudTrail to record transit gateway attachment, route table, association, and propagation changes for audit and unauthorized-change detection, and you MUST enable encryption at rest on the CloudTrail destination (a KMS key)
• You MUST, when a KMS key encrypts a flow log destination (CloudWatch log group or S3 bucket) or the CloudTrail destination, scope the KMS key policy with condition keys (aws:SourceArn, aws:SourceAccount, and kms:ViaService) so only the specific log group, bucket, or trail in the expected account and service can use the key, preventing cross-account or cross-service misuse
• You SHOULD create CloudWatch alarms for transit gateway attachment creation and deletion, route table changes, and failed or blocked attachment states, so that unexpected or unauthorized changes and failure conditions are surfaced for investigation rather than discovered after impact

2. Create the VPN attachment (VPN path)

Constraints:

• You MUST create the Site-to-Site VPN attached to the transit gateway, with the chosen routing and accelerated option (a single call creates both the VPN connection and the transit gateway VPN attachment). You MUST set tunnel options that enforce strong encryption (IKEv2 with AES-256 and AES256-GCM-16) rather than relying on AWS defaults, which may permit weaker ciphers. Phase 1 uses AES-256-CBC, which is not AEAD, so you MUST also pin Phase1IntegrityAlgorithms and Phase1DHGroupNumbers (otherwise AWS fills them in and may permit SHA-1 or weak Diffie-Hellman groups such as Group 2); Phase 2’s AES256-GCM-16 is AEAD and needs no separate integrity algorithm, but pin Phase2DHGroupNumbers for forward secrecy:

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  aws ec2 create-vpn-connection --type ipsec.1 \
    --customer-gateway-id {customer_gateway_id} \
    --transit-gateway-id {transit_gateway_id} \
    --options "EnableAcceleration={accelerated},StaticRoutesOnly={static_only},TunnelOptions=[{IKEVersions=[{Value=ikev2}],Phase1EncryptionAlgorithms=[{Value=AES256}],Phase1IntegrityAlgorithms=[{Value=SHA2-512}],Phase1DHGroupNumbers=[{Value=20}],Phase2EncryptionAlgorithms=[{Value=AES256-GCM-16}],Phase2DHGroupNumbers=[{Value=20}]},{IKEVersions=[{Value=ikev2}],Phase1EncryptionAlgorithms=[{Value=AES256}],Phase1IntegrityAlgorithms=[{Value=SHA2-512}],Phase1DHGroupNumbers=[{Value=20}],Phase2EncryptionAlgorithms=[{Value=AES256-GCM-16}],Phase2DHGroupNumbers=[{Value=20}]}]" \
    --region {region}

• You MUST capture the VpnConnectionId from the response

• You MUST poll until the VPN connection reaches available:

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  aws ec2 describe-vpn-connections \
    --vpn-connection-ids {vpn_connection_id} --region {region}

• You MUST add static routes to the transit gateway route table when vpn_routing is static

• You MUST, when a customer-specified pre-shared key (PSK) is used for an IPsec tunnel (via TunnelOptions[].PreSharedKey), store and retrieve it from AWS Secrets Manager, never hardcoding it in scripts or configuration files. Prefer the AWS-generated PSK when the customer has no requirement for a specific value

• You SHOULD enable Site-to-Site VPN tunnel logging to CloudWatch Logs for visibility into tunnel state changes, IKE negotiation failures, and dead peer detection events, which are critical for troubleshooting connectivity and detecting unauthorized connection attempts. These logs carry connection state and IKE negotiation detail, so you MUST enable encryption (a KMS key) on the destination CloudWatch log group

3. Associate the Direct Connect gateway (Direct Connect path)

Constraints:

• You MUST create the association from the transit gateway to the Direct Connect gateway the directconnect skill set up:

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  aws directconnect create-direct-connect-gateway-association \
    --direct-connect-gateway-id {dx_gateway_id} \
    --gateway-id {transit_gateway_id} \
    --add-allowed-prefixes-to-direct-connect-gateway cidr={allowed_prefix} --region {region}

• You MUST poll the association state until it reaches associated (this is an async operation that can take several minutes):

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  aws directconnect describe-direct-connect-gateway-associations \
    --direct-connect-gateway-id {dx_gateway_id} --region {region}

• You MUST NOT configure the Direct Connect gateway or virtual interface here

4. Wire association and propagation

Constraints:

• You MUST associate the attachment with the route table whose VPCs should reach on-premises, and propagate on-premises routes into the tables that need them
• You MUST verify the on-premises prefixes reach the intended attachments

5. Confirm and surface the console link

Constraints:

• You MUST confirm the attachment is available:

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  aws ec2 describe-transit-gateway-attachments \
    --filters Name=transit-gateway-id,Values={transit_gateway_id} --region {region}

• You MUST present the transit gateway console link, filling {transit_gateway_id} and {region} from the API response, and tell the customer to open it and verify the attachment and routes:

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  https://{region}.console.aws.amazon.com/vpc/home?region={region}#TransitGatewayDetails:transitGatewayId={transit_gateway_id}

Example

Example input

Example output

Troubleshooting

Tunnels do not aggregate bandwidth

ECMP needs BGP and tunnels on one transit gateway. Confirm both (ECMP across multiple tunnels).

Poor VPN performance

Accelerated VPN was not enabled at creation. Recreate with the accelerated option (Step 2).

On-premises routes missing from a VPC

Association or propagation is wrong. Fix the wiring (Step 4).

Additional Resources

• AWS Site-to-Site VPN attachments in AWS Transit Gateway (AWS Transit Gateway Guide) (opens in a new tab)
• Create a transit gateway attachment to a VPN in AWS Transit Gateway (AWS Transit Gateway Guide) (opens in a new tab)
• Accelerated Site-to-Site VPN connections (AWS Site-to-Site VPN User Guide) (opens in a new tab)
• Transit gateway attachments to a Direct Connect gateway in AWS Transit Gateway (AWS Transit Gateway Guide) (opens in a new tab)

Nearby

• PreviousReference Centralizing Egress And Inspection
• NextReference Creating A Transit Gateway And Attaching Vpcs