diff --git a/.backportrc.json b/.backportrc.json
index 358c26a0..464a447a 100644
--- a/.backportrc.json
+++ b/.backportrc.json
@@ -9,7 +9,8 @@
   "targetBranchChoices": [
     "main",
     "maintenance/v5.4",
-    "maintenance/v5.5"
+    "maintenance/v5.5",
+    "maintenance/v5.6"
   ],
   "//": "~~ Generated by projen. To modify, edit .projenrc.ts and run \"npx projen\"."
 }
diff --git a/.gitattributes b/.gitattributes
index 0a695bae..316848e3 100644
--- a/.gitattributes
+++ b/.gitattributes
@@ -10,9 +10,11 @@
 /.github/workflows/auto-merge.yml linguist-generated
 /.github/workflows/auto-tag-dev-v5.4.yml linguist-generated
 /.github/workflows/auto-tag-dev-v5.5.yml linguist-generated
+/.github/workflows/auto-tag-dev-v5.6.yml linguist-generated
 /.github/workflows/auto-tag-dev.yml linguist-generated
 /.github/workflows/auto-tag-releases-v5.4.yml linguist-generated
 /.github/workflows/auto-tag-releases-v5.5.yml linguist-generated
+/.github/workflows/auto-tag-releases-v5.6.yml linguist-generated
 /.github/workflows/auto-tag-releases.yml linguist-generated
 /.github/workflows/backport.yml linguist-generated
 /.github/workflows/build.yml linguist-generated
@@ -21,6 +23,7 @@
 /.github/workflows/upgrade-main.yml linguist-generated
 /.github/workflows/upgrade-maintenance-v5.4.yml linguist-generated
 /.github/workflows/upgrade-maintenance-v5.5.yml linguist-generated
+/.github/workflows/upgrade-maintenance-v5.6.yml linguist-generated
 /.gitignore linguist-generated
 /.npmignore linguist-generated
 /.prettierrc.json linguist-generated
diff --git a/.github/workflows/auto-tag-dev-v5.6.yml b/.github/workflows/auto-tag-dev-v5.6.yml
new file mode 100644
index 00000000..755b3802
--- /dev/null
+++ b/.github/workflows/auto-tag-dev-v5.6.yml
@@ -0,0 +1,59 @@
+# ~~ Generated by projen. To modify, edit .projenrc.ts and run "npx projen".
+
+name: auto-tag-dev-v5.6
+run-name: Auto-Tag Prerelease (v5.6)
+on:
+  schedule:
+    - cron: 0 15 * * 0,2-6
+  workflow_dispatch: {}
+jobs:
+  pre-flight:
+    name: Pre-Flight Checks
+    runs-on: ubuntu-latest
+    permissions:
+      contents: read
+    outputs:
+      sha: ${{ steps.git.outputs.sha }}
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+        with:
+          repository: ${{ github.repository }}
+          ref: maintenance/v5.6
+      - name: Setup Node.js
+        uses: actions/setup-node@v4
+        with:
+          cache: yarn
+          node-version: "18"
+      - name: Install dependencies
+        run: yarn install --frozen-lockfile
+      - name: Build
+        run: yarn build
+      - name: Identify git SHA
+        id: git
+        run: echo sha=$(git rev-parse HEAD) >> $GITHUB_OUTPUT
+  auto-tag:
+    name: Auto-Tag Release
+    needs: pre-flight
+    runs-on: ubuntu-latest
+    permissions: {}
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+        with:
+          repository: ${{ github.repository }}
+          token: ${{ secrets.PROJEN_GITHUB_TOKEN }}
+          ref: ${{ needs.pre-flight.outputs.sha }}
+      - name: Setup Node.js
+        uses: actions/setup-node@v4
+        with:
+          cache: yarn
+          node-version: "18"
+      - name: Install dependencies
+        run: yarn install --frozen-lockfile
+      - name: Set git identity
+        run: |-
+          git config user.name "github-actions"
+          git config user.email "github-actions@github.com"
+      - name: Tag PreRelease
+        run: yarn tag-release --idempotent --no-sign --push --prerelease=dev --release-line=5.6
diff --git a/.github/workflows/auto-tag-dev.yml b/.github/workflows/auto-tag-dev.yml
index b4d42cb2..13bdc686 100644
--- a/.github/workflows/auto-tag-dev.yml
+++ b/.github/workflows/auto-tag-dev.yml
@@ -56,4 +56,4 @@ jobs:
           git config user.name "github-actions"
           git config user.email "github-actions@github.com"
       - name: Tag PreRelease
-        run: yarn tag-release --idempotent --no-sign --push --prerelease=dev --release-line=5.6
+        run: yarn tag-release --idempotent --no-sign --push --prerelease=dev --release-line=5.7
diff --git a/.github/workflows/auto-tag-releases-v5.6.yml b/.github/workflows/auto-tag-releases-v5.6.yml
new file mode 100644
index 00000000..a11d391a
--- /dev/null
+++ b/.github/workflows/auto-tag-releases-v5.6.yml
@@ -0,0 +1,59 @@
+# ~~ Generated by projen. To modify, edit .projenrc.ts and run "npx projen".
+
+name: auto-tag-releases-v5.6
+run-name: Auto-Tag Release (v5.6)
+on:
+  schedule:
+    - cron: 0 15 * * 1
+  workflow_dispatch: {}
+jobs:
+  pre-flight:
+    name: Pre-Flight Checks
+    runs-on: ubuntu-latest
+    permissions:
+      contents: read
+    outputs:
+      sha: ${{ steps.git.outputs.sha }}
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+        with:
+          repository: ${{ github.repository }}
+          ref: maintenance/v5.6
+      - name: Setup Node.js
+        uses: actions/setup-node@v4
+        with:
+          cache: yarn
+          node-version: "18"
+      - name: Install dependencies
+        run: yarn install --frozen-lockfile
+      - name: Build
+        run: yarn build
+      - name: Identify git SHA
+        id: git
+        run: echo sha=$(git rev-parse HEAD) >> $GITHUB_OUTPUT
+  auto-tag:
+    name: Auto-Tag Release
+    needs: pre-flight
+    runs-on: ubuntu-latest
+    permissions: {}
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+        with:
+          repository: ${{ github.repository }}
+          token: ${{ secrets.PROJEN_GITHUB_TOKEN }}
+          ref: ${{ needs.pre-flight.outputs.sha }}
+      - name: Setup Node.js
+        uses: actions/setup-node@v4
+        with:
+          cache: yarn
+          node-version: "18"
+      - name: Install dependencies
+        run: yarn install --frozen-lockfile
+      - name: Set git identity
+        run: |-
+          git config user.name "github-actions"
+          git config user.email "github-actions@github.com"
+      - name: Tag Release
+        run: yarn tag-release --idempotent --no-sign --push --release-line=5.6
diff --git a/.github/workflows/auto-tag-releases.yml b/.github/workflows/auto-tag-releases.yml
index efce2a93..b395e680 100644
--- a/.github/workflows/auto-tag-releases.yml
+++ b/.github/workflows/auto-tag-releases.yml
@@ -56,4 +56,4 @@ jobs:
           git config user.name "github-actions"
           git config user.email "github-actions@github.com"
       - name: Tag Release
-        run: yarn tag-release --idempotent --no-sign --push --release-line=5.6
+        run: yarn tag-release --idempotent --no-sign --push --release-line=5.7
diff --git a/.github/workflows/upgrade-maintenance-v5.6.yml b/.github/workflows/upgrade-maintenance-v5.6.yml
new file mode 100644
index 00000000..3671992e
--- /dev/null
+++ b/.github/workflows/upgrade-maintenance-v5.6.yml
@@ -0,0 +1,97 @@
+# ~~ Generated by projen. To modify, edit .projenrc.ts and run "npx projen".
+
+name: upgrade-maintenance-v5.6
+on:
+  workflow_dispatch: {}
+  schedule:
+    - cron: 0 0 * * *
+jobs:
+  upgrade:
+    name: Upgrade
+    runs-on: ubuntu-latest
+    permissions:
+      contents: read
+    outputs:
+      patch_created: ${{ steps.create_patch.outputs.patch_created }}
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+        with:
+          ref: maintenance/v5.6
+      - name: Setup Node.js
+        uses: actions/setup-node@v4
+        with:
+          node-version: lts/*
+      - name: Install dependencies
+        run: yarn install --check-files --frozen-lockfile
+      - name: Back-port projenrc changes from main
+        env:
+          CI: "false"
+        run: git fetch origin main && git checkout FETCH_HEAD -- README.md && yarn projen
+      - name: Upgrade dependencies
+        run: npx projen upgrade
+      - name: Find mutations
+        id: create_patch
+        run: |-
+          git add .
+          git diff --staged --patch --exit-code > repo.patch || echo "patch_created=true" >> $GITHUB_OUTPUT
+        working-directory: ./
+      - name: Upload patch
+        if: steps.create_patch.outputs.patch_created
+        uses: actions/upload-artifact@v4.4.0
+        with:
+          name: repo.patch
+          path: repo.patch
+          overwrite: true
+  pr:
+    name: Create Pull Request
+    needs: upgrade
+    runs-on: ubuntu-latest
+    permissions:
+      contents: read
+    if: ${{ needs.upgrade.outputs.patch_created }}
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v4
+        with:
+          ref: maintenance/v5.6
+      - name: Download patch
+        uses: actions/download-artifact@v4
+        with:
+          name: repo.patch
+          path: ${{ runner.temp }}
+      - name: Apply patch
+        run: '[ -s ${{ runner.temp }}/repo.patch ] && git apply ${{ runner.temp }}/repo.patch || echo "Empty patch. Skipping."'
+      - name: Set git identity
+        run: |-
+          git config user.name "github-actions"
+          git config user.email "github-actions@github.com"
+      - name: Create Pull Request
+        id: create-pr
+        uses: peter-evans/create-pull-request@v6
+        with:
+          token: ${{ secrets.PROJEN_GITHUB_TOKEN }}
+          commit-message: |-
+            chore(deps): upgrade dependencies
+
+            Upgrades project dependencies. See details in [workflow run].
+
+            [Workflow Run]: ${{ github.server_url }}/${{ github.repository }}/actions/runs/${{ github.run_id }}
+
+            ------
+
+            *Automatically created by projen via the "upgrade-maintenance-v5.6" workflow*
+          branch: github-actions/upgrade-maintenance-v5.6
+          title: "chore(deps): upgrade dependencies"
+          labels: auto-approve
+          body: |-
+            Upgrades project dependencies. See details in [workflow run].
+
+            [Workflow Run]: ${{ github.server_url }}/${{ github.repository }}/actions/runs/${{ github.run_id }}
+
+            ------
+
+            *Automatically created by projen via the "upgrade-maintenance-v5.6" workflow*
+          author: github-actions <github-actions@github.com>
+          committer: github-actions <github-actions@github.com>
+          signoff: true
diff --git a/.gitignore b/.gitignore
index 2e0ac6a3..7475af89 100644
--- a/.gitignore
+++ b/.gitignore
@@ -45,6 +45,7 @@ jspm_packages/
 !/.github/workflows/upgrade-main.yml
 !/.github/workflows/upgrade-maintenance-v5.4.yml
 !/.github/workflows/upgrade-maintenance-v5.5.yml
+!/.github/workflows/upgrade-maintenance-v5.6.yml
 /build-tools/tsconfig.json
 /projenrc/tsconfig.json
 /test/tsconfig.json
@@ -63,6 +64,8 @@ jspm_packages/
 !/.github/workflows/auto-tag-releases-v5.4.yml
 !/.github/workflows/auto-tag-dev-v5.5.yml
 !/.github/workflows/auto-tag-releases-v5.5.yml
+!/.github/workflows/auto-tag-dev-v5.6.yml
+!/.github/workflows/auto-tag-releases-v5.6.yml
 !/.backportrc.json
 !/.github/workflows/backport.yml
 !/.projenrc.ts
diff --git a/.projen/deps.json b/.projen/deps.json
index b0159208..20bfbb50 100644
--- a/.projen/deps.json
+++ b/.projen/deps.json
@@ -182,7 +182,7 @@
     },
     {
       "name": "typescript",
-      "version": "~5.6",
+      "version": "~5.7",
       "type": "runtime"
     },
     {
diff --git a/.projen/files.json b/.projen/files.json
index 124bfbb6..131a036b 100644
--- a/.projen/files.json
+++ b/.projen/files.json
@@ -8,9 +8,11 @@
     ".github/workflows/auto-merge.yml",
     ".github/workflows/auto-tag-dev-v5.4.yml",
     ".github/workflows/auto-tag-dev-v5.5.yml",
+    ".github/workflows/auto-tag-dev-v5.6.yml",
     ".github/workflows/auto-tag-dev.yml",
     ".github/workflows/auto-tag-releases-v5.4.yml",
     ".github/workflows/auto-tag-releases-v5.5.yml",
+    ".github/workflows/auto-tag-releases-v5.6.yml",
     ".github/workflows/auto-tag-releases.yml",
     ".github/workflows/backport.yml",
     ".github/workflows/build.yml",
@@ -19,6 +21,7 @@
     ".github/workflows/upgrade-main.yml",
     ".github/workflows/upgrade-maintenance-v5.4.yml",
     ".github/workflows/upgrade-maintenance-v5.5.yml",
+    ".github/workflows/upgrade-maintenance-v5.6.yml",
     ".gitignore",
     ".npmignore",
     ".prettierrc.json",
diff --git a/.projenrc.ts b/.projenrc.ts
index 93792e00..c7b08d7c 100644
--- a/.projenrc.ts
+++ b/.projenrc.ts
@@ -11,20 +11,18 @@ import { UpgradeDependencies } from './projenrc/upgrade-dependencies';
 //  1. Fork the current `main` to a maintenance branch:
 //     `git switch main && git fetch --all && git pull`
 //     `git push origin main:maintenance/vX.Y` (X.Y is the TS version that is about to be replaced by a new release)
-//  2. Add a branch protection rule for the new maintenance branch.
-//     Copy the settings from the most recent maintenance branch.
-//  3. Edit `projenrc/support.ts`, set maintenance EOL date for the new maintenance version to be 6 months from
+//  2. Edit `projenrc/support.ts`, set maintenance EOL date for the new maintenance version to be 6 months from
 //     today (round up to the mid-point or end of month), make the new version current.
-//  4. Update `minNodeVersion` to the oldest LTS version of Node (i.e. dropping support for EOL versions of Node)
-//  5. Update the version list in the README (remember to remove EOS versions)
-//  6. If any versions dropped into EOS, change the respective branch protection rule to include "Lock branch"
-//  7. `npx projen`
-//  8. `npx projen build` and resolve any new test failures that might be introduced by the new TS version
-//  9. Create a PR, with title "feat: TypeScript X.Y"
-// 10. Note that merging the PR doesn't trigger a release. Release are performed on a weekly schedule.
+//  3. Update `minNodeVersion` to the oldest LTS version of Node (i.e. dropping support for EOL versions of Node)
+//  4. Update the version list in the README (remember to remove EOS versions)
+//  5. If any versions dropped into EOS, add the respective branch to the "end-of-support" ruleset.
+//  6. `npx projen`
+//  7. `npx projen build` and resolve any new test failures that might be introduced by the new TS version
+//  8. Create a PR, with title "feat: TypeScript X.Y"
+//  9. Note that merging the PR doesn't trigger a release. Release are performed on a weekly schedule.
 //     You need to manually create a release by triggering this workflow:
 //     https://github.com/aws/jsii-compiler/actions/workflows/auto-tag-releases.yml
-// 11. Perform new version steps for `jsii-rosetta`
+// 10. Perform new version steps for `jsii-rosetta`
 
 const project = new typescript.TypeScriptProject({
   projenrcTs: true,
diff --git a/README.md b/README.md
index 3925e5ea..3707fdc7 100644
--- a/README.md
+++ b/README.md
@@ -64,7 +64,8 @@ The current status of `jsii` compiler releases is:
 
 | Release | Status      | EOS        | Comment                                                                                 |
 | ------- | ----------- | ---------- | --------------------------------------------------------------------------------------- |
-| `5.6.x` | Current     | TBD        | ![npm](https://img.shields.io/npm/v/jsii/v5.6-latest?label=jsii%40v5.6-latest&logo=npm) |
+| `5.7.x` | Current     | TBD        | ![npm](https://img.shields.io/npm/v/jsii/v5.7-latest?label=jsii%40v5.7-latest&logo=npm) |
+| `5.6.x` | Maintenance | 2025-07-01 | ![npm](https://img.shields.io/npm/v/jsii/v5.6-latest?label=jsii%40v5.6-latest&logo=npm) |
 | `5.5.x` | Maintenance | 2025-05-15 | ![npm](https://img.shields.io/npm/v/jsii/v5.5-latest?label=jsii%40v5.5-latest&logo=npm) |
 | `5.4.x` | Maintenance | 2025-02-28 | ![npm](https://img.shields.io/npm/v/jsii/v5.4-latest?label=jsii%40v5.4-latest&logo=npm) |
 
diff --git a/package.json b/package.json
index 9793403a..78ce4987 100644
--- a/package.json
+++ b/package.json
@@ -80,7 +80,7 @@
     "semver-intersect": "^1.5.0",
     "sort-json": "^2.0.1",
     "spdx-license-list": "^6.9.0",
-    "typescript": "~5.6",
+    "typescript": "~5.7",
     "yargs": "^17.7.2"
   },
   "engines": {
diff --git a/projenrc/support.ts b/projenrc/support.ts
index db5c38aa..42893610 100644
--- a/projenrc/support.ts
+++ b/projenrc/support.ts
@@ -2,7 +2,7 @@ import { JsonFile, Project } from 'projen';
 import type { ReleasesDocument } from '../src/support';
 
 export const SUPPORT_POLICY: ReleasesDocument = {
-  current: '5.6',
+  current: '5.7',
   maintenance: {
     // version: End-of-support date
     '5.0': new Date('2024-01-31'),
@@ -11,6 +11,7 @@ export const SUPPORT_POLICY: ReleasesDocument = {
     '5.3': new Date('2024-10-15'),
     '5.4': new Date('2025-02-28'),
     '5.5': new Date('2025-05-15'),
+    '5.6': new Date('2025-07-01'),
   },
 };
 
diff --git a/releases.json b/releases.json
index 1cac1b0c..0e80b551 100644
--- a/releases.json
+++ b/releases.json
@@ -1,12 +1,13 @@
 {
-  "current": "5.6",
+  "current": "5.7",
   "maintenance": {
     "5.0": "2024-01-31T00:00:00.000Z",
     "5.1": "2024-02-28T00:00:00.000Z",
     "5.2": "2024-06-30T00:00:00.000Z",
     "5.3": "2024-10-15T00:00:00.000Z",
     "5.4": "2025-02-28T00:00:00.000Z",
-    "5.5": "2025-05-15T00:00:00.000Z"
+    "5.5": "2025-05-15T00:00:00.000Z",
+    "5.6": "2025-07-01T00:00:00.000Z"
   },
   "//": "~~ Generated by projen. To modify, edit .projenrc.ts and run \"npx projen\"."
 }
diff --git a/src/tsconfig/validator.ts b/src/tsconfig/validator.ts
index 33f08637..9a32d201 100644
--- a/src/tsconfig/validator.ts
+++ b/src/tsconfig/validator.ts
@@ -192,6 +192,12 @@ function wrapMatcher(matcher: Matcher, message: (actual: any) => string, allowed
  */
 function looseEqual(a: any, b: any): boolean {
   try {
+    // if one of the values is an object (or array), but the other isn't - never consider them the same
+    if ([typeof a, typeof b].filter((t) => t === 'object').length === 1) {
+      return false;
+    }
+    // if both values are the same object
+    // or if both values are loose equal
     return Object.is(a, b) || a == b;
   } catch {
     return false;
diff --git a/test/compiler.test.ts b/test/compiler.test.ts
index aeeb2507..d257a28a 100644
--- a/test/compiler.test.ts
+++ b/test/compiler.test.ts
@@ -107,7 +107,7 @@ describe(Compiler, () => {
       } finally {
         rmSync(sourceDir, { force: true, recursive: true });
       }
-    }, 15_000);
+    }, 25_000);
 
     test('rootDir is added to assembly', () => {
       const outDir = 'jsii-outdir';
@@ -336,7 +336,7 @@ describe(Compiler, () => {
       } finally {
         rmSync(sourceDir, { force: true, recursive: true });
       }
-    }, 15_000);
+    }, 25_000);
   });
 
   describe('compressed assembly option', () => {
diff --git a/test/tsconfig/helpers.ts b/test/tsconfig/helpers.ts
index 9987d508..64a67ab7 100644
--- a/test/tsconfig/helpers.ts
+++ b/test/tsconfig/helpers.ts
@@ -192,6 +192,8 @@ export function fcTsconfig(
     isolatedDeclarations: fc.boolean(),
     strictBuiltinIteratorReturn: fc.boolean(),
     noUncheckedSideEffectImports: fc.boolean(),
+    noCheck: fc.boolean(),
+    rewriteRelativeImportExtensions: fc.boolean(),
   };
 
   // limit to only allowed keys
diff --git a/yarn.lock b/yarn.lock
index f226dc9e..d58f2d6b 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -6491,10 +6491,10 @@ typescript@~3.9.10:
   resolved "https://registry.yarnpkg.com/typescript/-/typescript-3.9.10.tgz#70f3910ac7a51ed6bef79da7800690b19bf778b8"
   integrity sha512-w6fIxVE/H1PkLKcCPsFqKE7Kv7QUwhU8qQY2MueZXWx5cPZdwFupLgKK3vntcK98BtNHZtAF4LA/yl2a7k8R6Q==
 
-typescript@~5.6:
-  version "5.6.3"
-  resolved "https://registry.yarnpkg.com/typescript/-/typescript-5.6.3.tgz#5f3449e31c9d94febb17de03cc081dd56d81db5b"
-  integrity sha512-hjcS1mhfuyi4WW8IWtjP7brDrG2cuDZukyrYrSauoXGNgx0S7zceP07adYkJycEr56BOUTNPzbInooiN3fn1qw==
+typescript@~5.7:
+  version "5.7.2"
+  resolved "https://registry.yarnpkg.com/typescript/-/typescript-5.7.2.tgz#3169cf8c4c8a828cde53ba9ecb3d2b1d5dd67be6"
+  integrity sha512-i5t66RHxDvVN40HfDd1PsEThGNnlMCMT3jMUuoh9/0TaqWevNontacunWyN02LA9/fIbEWlcHZcgTKb9QoaLfg==
 
 unbox-primitive@^1.0.2:
   version "1.0.2"