diff --git a/package-lock.json b/package-lock.json
index 87b0829b5..62c965355 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -6959,6 +6959,25 @@
         "@lezer/common": "^1.0.0"
       }
     },
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+      "resolved": "https://registry.npmjs.org/@lukeed/csprng/-/csprng-1.1.0.tgz",
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+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/@lukeed/uuid": {
+      "version": "2.0.1",
+      "resolved": "https://registry.npmjs.org/@lukeed/uuid/-/uuid-2.0.1.tgz",
+      "integrity": "sha512-qC72D4+CDdjGqJvkFMMEAtancHUQ7/d/tAiHf64z8MopFDmcrtbcJuerDtFceuAfQJ2pDSfCKCtbqoGBNnwg0w==",
+      "dependencies": {
+        "@lukeed/csprng": "^1.1.0"
+      },
+      "engines": {
+        "node": ">=8"
+      }
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       "version": "1.8.0",
       "resolved": "https://registry.npmjs.org/@mongodb-js/compass-components/-/compass-components-1.8.0.tgz",
@@ -9444,15 +9463,98 @@
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-      "resolved": "https://registry.npmjs.org/@segment/loosely-validate-event/-/loosely-validate-event-2.0.0.tgz",
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+    "node_modules/@segment/analytics-core": {
+      "version": "1.4.1",
+      "resolved": "https://registry.npmjs.org/@segment/analytics-core/-/analytics-core-1.4.1.tgz",
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+    "node_modules/@segment/analytics-core/node_modules/tslib": {
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+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.6.2.tgz",
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+    },
+    "node_modules/@segment/analytics-generic-utils": {
+      "version": "1.1.1",
+      "resolved": "https://registry.npmjs.org/@segment/analytics-generic-utils/-/analytics-generic-utils-1.1.1.tgz",
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+      "dependencies": {
+        "tslib": "^2.4.1"
+      }
+    },
+    "node_modules/@segment/analytics-generic-utils/node_modules/tslib": {
+      "version": "2.6.2",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.6.2.tgz",
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+    },
+    "node_modules/@segment/analytics-node": {
+      "version": "1.3.0",
+      "resolved": "https://registry.npmjs.org/@segment/analytics-node/-/analytics-node-1.3.0.tgz",
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       "dependencies": {
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-        "join-component": "^1.1.0"
+        "@lukeed/uuid": "^2.0.0",
+        "@segment/analytics-core": "1.4.1",
+        "@segment/analytics-generic-utils": "1.1.1",
+        "buffer": "^6.0.3",
+        "node-fetch": "^2.6.7",
+        "tslib": "^2.4.1"
+      },
+      "engines": {
+        "node": ">=14"
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+    "node_modules/@segment/analytics-node/node_modules/buffer": {
+      "version": "6.0.3",
+      "resolved": "https://registry.npmjs.org/buffer/-/buffer-6.0.3.tgz",
+      "integrity": "sha512-FTiCpNxtwiZZHEZbcbTIcZjERVICn9yq/pDFkTl95/AxzD1naBctN7YO68riM/gLSDY7sdrMby8hofADYuuqOA==",
+      "funding": [
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/feross"
+        },
+        {
+          "type": "patreon",
+          "url": "https://www.patreon.com/feross"
+        },
+        {
+          "type": "consulting",
+          "url": "https://feross.org/support"
+        }
+      ],
+      "dependencies": {
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+        "ieee754": "^1.2.1"
+      }
+    },
+    "node_modules/@segment/analytics-node/node_modules/ieee754": {
+      "version": "1.2.1",
+      "resolved": "https://registry.npmjs.org/ieee754/-/ieee754-1.2.1.tgz",
+      "integrity": "sha512-dcyqhDvX1C46lXZcVqCpK+FtMRQVdIMN6/Df5js2zouUsqG7I6sFxitIC+7KYK29KdXOLHdu9zL4sFnoVQnqaA==",
+      "funding": [
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/feross"
+        },
+        {
+          "type": "patreon",
+          "url": "https://www.patreon.com/feross"
+        },
+        {
+          "type": "consulting",
+          "url": "https://feross.org/support"
+        }
+      ]
+    },
+    "node_modules/@segment/analytics-node/node_modules/tslib": {
+      "version": "2.6.2",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.6.2.tgz",
+      "integrity": "sha512-AEYxH93jGFPn/a2iVAwW87VuUIkR1FVUKB77NwMF7nBTDkDrrT/Hpt/IrCJ0QXhW27jTBDcf5ZY7w6RiqTMw2Q=="
+    },
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       "resolved": "https://registry.npmjs.org/@sideway/address/-/address-4.1.4.tgz",
@@ -9727,12 +9829,6 @@
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-      "resolved": "https://registry.npmjs.org/@types/analytics-node/-/analytics-node-3.1.10.tgz",
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@@ -11096,32 +11192,6 @@
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-      "resolved": "https://registry.npmjs.org/analytics-node/-/analytics-node-5.1.2.tgz",
-      "integrity": "sha512-WZ8gkXtLuqD2Q2xEOr/2/LJiR0AnhWHfXZhfPnMZpB7vEwCsh3HapYAUmA1cPj1abrhAqBX7POWuWo/1wUu/Fw==",
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@@ -11621,22 +11691,6 @@
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-      "resolved": "https://registry.npmjs.org/axios-retry/-/axios-retry-3.2.0.tgz",
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@@ -12567,14 +12621,6 @@
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-      "resolved": "https://registry.npmjs.org/charenc/-/charenc-0.0.2.tgz",
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@@ -12957,11 +13003,6 @@
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@@ -13443,14 +13484,6 @@
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@@ -14425,6 +14458,14 @@
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+      "resolved": "https://registry.npmjs.org/dset/-/dset-3.1.3.tgz",
+      "integrity": "sha512-20TuZZHCEZ2O71q9/+8BwKwZ0QtD9D8ObhrihJPr+vLLYlSuAU3/zL4cSlgbfeoGHTjCSJBa7NGcrF9/Bx/WJQ==",
+      "engines": {
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+      }
+    },
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+      "devOptional": true,
       "funding": [
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@@ -17893,11 +17935,6 @@
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+      "dev": true
     },
     "node_modules/lodash.memoize": {
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@@ -21831,16 +21864,6 @@
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-      "resolved": "https://registry.npmjs.org/md5/-/md5-2.3.0.tgz",
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-        "analytics-node": "^5.1.2",
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@@ -30920,7 +30938,6 @@
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@@ -37015,6 +37032,19 @@
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       }
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+    "@lukeed/csprng": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/@lukeed/csprng/-/csprng-1.1.0.tgz",
+      "integrity": "sha512-Z7C/xXCiGWsg0KuKsHTKJxbWhpI3Vs5GwLfOean7MGyVFGqdRgBbAjOCh6u4bbjPc/8MJ2pZmK/0DLdCbivLDA=="
+    },
+    "@lukeed/uuid": {
+      "version": "2.0.1",
+      "resolved": "https://registry.npmjs.org/@lukeed/uuid/-/uuid-2.0.1.tgz",
+      "integrity": "sha512-qC72D4+CDdjGqJvkFMMEAtancHUQ7/d/tAiHf64z8MopFDmcrtbcJuerDtFceuAfQJ2pDSfCKCtbqoGBNnwg0w==",
+      "requires": {
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@@ -37744,7 +37774,6 @@
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@@ -39512,13 +39541,71 @@
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+    "@segment/analytics-core": {
+      "version": "1.4.1",
+      "resolved": "https://registry.npmjs.org/@segment/analytics-core/-/analytics-core-1.4.1.tgz",
+      "integrity": "sha512-kV0Pf33HnthuBOVdYNani21kYyj118Fn+9757bxqoksiXoZlYvBsFq6giNdCsKcTIE1eAMqNDq3xE1VQ0cfsHA==",
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-        "component-type": "^1.2.1",
-        "join-component": "^1.1.0"
+        "@lukeed/uuid": "^2.0.0",
+        "@segment/analytics-generic-utils": "1.1.1",
+        "dset": "^3.1.2",
+        "tslib": "^2.4.1"
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+        }
+      }
+    },
+    "@segment/analytics-generic-utils": {
+      "version": "1.1.1",
+      "resolved": "https://registry.npmjs.org/@segment/analytics-generic-utils/-/analytics-generic-utils-1.1.1.tgz",
+      "integrity": "sha512-THTIzBPHnvu1HYJU3fARdJ3qIkukO3zDXsmDm+kAeUks5R9CBXOQ6rPChiASVzSmwAIIo5uFIXXnCraojlq/Gw==",
+      "requires": {
+        "tslib": "^2.4.1"
+      },
+      "dependencies": {
+        "tslib": {
+          "version": "2.6.2",
+          "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.6.2.tgz",
+          "integrity": "sha512-AEYxH93jGFPn/a2iVAwW87VuUIkR1FVUKB77NwMF7nBTDkDrrT/Hpt/IrCJ0QXhW27jTBDcf5ZY7w6RiqTMw2Q=="
+        }
+      }
+    },
+    "@segment/analytics-node": {
+      "version": "1.3.0",
+      "resolved": "https://registry.npmjs.org/@segment/analytics-node/-/analytics-node-1.3.0.tgz",
+      "integrity": "sha512-lRLz1WZaDokMoUe299yP5JkInc3OgJuqNNlxb6j0q22umCiq6b5iDo2gRmFn93reirIvJxWIicQsGrHd93q8GQ==",
+      "requires": {
+        "@lukeed/uuid": "^2.0.0",
+        "@segment/analytics-core": "1.4.1",
+        "@segment/analytics-generic-utils": "1.1.1",
+        "buffer": "^6.0.3",
+        "node-fetch": "^2.6.7",
+        "tslib": "^2.4.1"
+      },
+      "dependencies": {
+        "buffer": {
+          "version": "6.0.3",
+          "resolved": "https://registry.npmjs.org/buffer/-/buffer-6.0.3.tgz",
+          "integrity": "sha512-FTiCpNxtwiZZHEZbcbTIcZjERVICn9yq/pDFkTl95/AxzD1naBctN7YO68riM/gLSDY7sdrMby8hofADYuuqOA==",
+          "requires": {
+            "base64-js": "^1.3.1",
+            "ieee754": "^1.2.1"
+          }
+        },
+        "ieee754": {
+          "version": "1.2.1",
+          "resolved": "https://registry.npmjs.org/ieee754/-/ieee754-1.2.1.tgz",
+          "integrity": "sha512-dcyqhDvX1C46lXZcVqCpK+FtMRQVdIMN6/Df5js2zouUsqG7I6sFxitIC+7KYK29KdXOLHdu9zL4sFnoVQnqaA=="
+        },
+        "tslib": {
+          "version": "2.6.2",
+          "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.6.2.tgz",
+          "integrity": "sha512-AEYxH93jGFPn/a2iVAwW87VuUIkR1FVUKB77NwMF7nBTDkDrrT/Hpt/IrCJ0QXhW27jTBDcf5ZY7w6RiqTMw2Q=="
+        }
       }
     },
     "@sideway/address": {
@@ -39764,12 +39851,6 @@
         }
       }
     },
-    "@types/analytics-node": {
-      "version": "3.1.10",
-      "resolved": "https://registry.npmjs.org/@types/analytics-node/-/analytics-node-3.1.10.tgz",
-      "integrity": "sha512-dvn8iy2EQZDlQGgRNT9SW2Ljn9L3VgwcrpJvonufnNygZWB1XEufXNvDhUtwNUqNyHhD0hbDCCFb9j+B7vE5cA==",
-      "dev": true
-    },
     "@types/ansi-escape-sequences": {
       "version": "4.0.0",
       "resolved": "https://registry.npmjs.org/@types/ansi-escape-sequences/-/ansi-escape-sequences-4.0.0.tgz",
@@ -40939,28 +41020,6 @@
       "dev": true,
       "requires": {}
     },
-    "analytics-node": {
-      "version": "5.1.2",
-      "resolved": "https://registry.npmjs.org/analytics-node/-/analytics-node-5.1.2.tgz",
-      "integrity": "sha512-WZ8gkXtLuqD2Q2xEOr/2/LJiR0AnhWHfXZhfPnMZpB7vEwCsh3HapYAUmA1cPj1abrhAqBX7POWuWo/1wUu/Fw==",
-      "requires": {
-        "@segment/loosely-validate-event": "^2.0.0",
-        "axios": "^0.21.4",
-        "axios-retry": "3.2.0",
-        "lodash.isstring": "^4.0.1",
-        "md5": "^2.2.1",
-        "ms": "^2.0.0",
-        "remove-trailing-slash": "^0.1.0",
-        "uuid": "^8.3.2"
-      },
-      "dependencies": {
-        "uuid": {
-          "version": "8.3.2",
-          "resolved": "https://registry.npmjs.org/uuid/-/uuid-8.3.2.tgz",
-          "integrity": "sha512-+NYs2QeMWy+GWFOEm9xnn6HCDp0l7QBD7ml8zLUmJ+93Q5NF0NocErnwkTkXVFNiX3/fpC6afS8Dhb/gz7R7eg=="
-        }
-      }
-    },
     "ansi-colors": {
       "version": "4.1.1",
       "resolved": "https://registry.npmjs.org/ansi-colors/-/ansi-colors-4.1.1.tgz",
@@ -41358,22 +41417,6 @@
       "resolved": "https://registry.npmjs.org/axe-core/-/axe-core-4.7.2.tgz",
       "integrity": "sha512-zIURGIS1E1Q4pcrMjp+nnEh+16G56eG/MUllJH8yEvw7asDo7Ac9uhC9KIH5jzpITueEZolfYglnCGIuSBz39g=="
     },
-    "axios": {
-      "version": "0.21.4",
-      "resolved": "https://registry.npmjs.org/axios/-/axios-0.21.4.tgz",
-      "integrity": "sha512-ut5vewkiu8jjGBdqpM44XxjuCjq9LAKeHVmoVfHVzy8eHgxxq8SbAVQNovDA8mVi05kP0Ea/n/UzcSHcTJQfNg==",
-      "requires": {
-        "follow-redirects": "^1.14.0"
-      }
-    },
-    "axios-retry": {
-      "version": "3.2.0",
-      "resolved": "https://registry.npmjs.org/axios-retry/-/axios-retry-3.2.0.tgz",
-      "integrity": "sha512-RK2cLMgIsAQBDhlIsJR5dOhODPigvel18XUv1dDXW+4k1FzebyfRk+C+orot6WPZOYFKSfhLwHPwVmTVOODQ5w==",
-      "requires": {
-        "is-retry-allowed": "^1.1.0"
-      }
-    },
     "axobject-query": {
       "version": "3.2.1",
       "resolved": "https://registry.npmjs.org/axobject-query/-/axobject-query-3.2.1.tgz",
@@ -42100,11 +42143,6 @@
       "integrity": "sha512-mT8iDcrh03qDGRRmoA2hmBJnxpllMR+0/0qlzjqZES6NdiWDcZkCNAk4rPFZ9Q85r27unkiNNg8ZOiwZXBHwcA==",
       "optional": true
     },
-    "charenc": {
-      "version": "0.0.2",
-      "resolved": "https://registry.npmjs.org/charenc/-/charenc-0.0.2.tgz",
-      "integrity": "sha512-yrLQ/yVUFXkzg7EDQsPieE/53+0RlaWTs+wBrvW36cyilJ2SaDWfl4Yj7MtLTXleV9uEKefbAGUPv2/iWSooRA=="
-    },
     "check-error": {
       "version": "1.0.2",
       "resolved": "https://registry.npmjs.org/check-error/-/check-error-1.0.2.tgz",
@@ -42399,11 +42437,6 @@
         "dot-prop": "^5.1.0"
       }
     },
-    "component-type": {
-      "version": "1.2.1",
-      "resolved": "https://registry.npmjs.org/component-type/-/component-type-1.2.1.tgz",
-      "integrity": "sha512-Kgy+2+Uwr75vAi6ChWXgHuLvd+QLD7ssgpaRq2zCvt80ptvAfMc/hijcJxXkBa2wMlEZcJvC2H8Ubo+A9ATHIg=="
-    },
     "compress-brotli": {
       "version": "1.3.8",
       "resolved": "https://registry.npmjs.org/compress-brotli/-/compress-brotli-1.3.8.tgz",
@@ -42807,11 +42840,6 @@
         "which": "^2.0.1"
       }
     },
-    "crypt": {
-      "version": "0.0.2",
-      "resolved": "https://registry.npmjs.org/crypt/-/crypt-0.0.2.tgz",
-      "integrity": "sha512-mCxBlsHFYh9C+HVpiEacem8FEBnMXgU9gy4zmNC+SXAZNB/1idgp/aulFJ4FgCi7GPEVbfyng092GqL2k2rmow=="
-    },
     "crypto-browserify": {
       "version": "3.12.0",
       "resolved": "https://registry.npmjs.org/crypto-browserify/-/crypto-browserify-3.12.0.tgz",
@@ -43550,6 +43578,11 @@
         "pify": "^4.0.1"
       }
     },
+    "dset": {
+      "version": "3.1.3",
+      "resolved": "https://registry.npmjs.org/dset/-/dset-3.1.3.tgz",
+      "integrity": "sha512-20TuZZHCEZ2O71q9/+8BwKwZ0QtD9D8ObhrihJPr+vLLYlSuAU3/zL4cSlgbfeoGHTjCSJBa7NGcrF9/Bx/WJQ=="
+    },
     "duplexer": {
       "version": "0.1.2",
       "resolved": "https://registry.npmjs.org/duplexer/-/duplexer-0.1.2.tgz",
@@ -44833,7 +44866,8 @@
     "follow-redirects": {
       "version": "1.15.4",
       "resolved": "https://registry.npmjs.org/follow-redirects/-/follow-redirects-1.15.4.tgz",
-      "integrity": "sha512-Cr4D/5wlrb0z9dgERpUL3LrmPKVDsETIJhaCMeDfuFYcqa5bldGV6wBsAN6X/vxlXQtFBMrXdXxdL8CbDTGniw=="
+      "integrity": "sha512-Cr4D/5wlrb0z9dgERpUL3LrmPKVDsETIJhaCMeDfuFYcqa5bldGV6wBsAN6X/vxlXQtFBMrXdXxdL8CbDTGniw==",
+      "devOptional": true
     },
     "for-each": {
       "version": "0.3.3",
@@ -46225,11 +46259,6 @@
         "has-tostringtag": "^1.0.0"
       }
     },
-    "is-buffer": {
-      "version": "1.1.6",
-      "resolved": "https://registry.npmjs.org/is-buffer/-/is-buffer-1.1.6.tgz",
-      "integrity": "sha512-NcdALwpXkTm5Zvvbk7owOUSvVvBKDgKP5/ewfXEznmQFfs4ZRmanOeKBTjRVjka3QFoN6XJ+9F3USqfHqTaU5w=="
-    },
     "is-callable": {
       "version": "1.2.7",
       "resolved": "https://registry.npmjs.org/is-callable/-/is-callable-1.2.7.tgz",
@@ -46747,11 +46776,6 @@
         "@sideway/pinpoint": "^2.0.0"
       }
     },
-    "join-component": {
-      "version": "1.1.0",
-      "resolved": "https://registry.npmjs.org/join-component/-/join-component-1.1.0.tgz",
-      "integrity": "sha512-bF7vcQxbODoGK1imE2P9GS9aw4zD0Sd+Hni68IMZLj7zRnquH7dXUmMw9hDI5S/Jzt7q+IyTXN0rSg2GI0IKhQ=="
-    },
     "jose": {
       "version": "4.14.4",
       "resolved": "https://registry.npmjs.org/jose/-/jose-4.14.4.tgz",
@@ -48836,7 +48860,8 @@
     "lodash.isstring": {
       "version": "4.0.1",
       "resolved": "https://registry.npmjs.org/lodash.isstring/-/lodash.isstring-4.0.1.tgz",
-      "integrity": "sha512-0wJxfxH1wgO3GrbuP+dTTk7op+6L41QCXbGINEmD+ny/G/eCqGzxyCsh7159S+mgDDcoarnBw6PC1PS5+wUGgw=="
+      "integrity": "sha512-0wJxfxH1wgO3GrbuP+dTTk7op+6L41QCXbGINEmD+ny/G/eCqGzxyCsh7159S+mgDDcoarnBw6PC1PS5+wUGgw==",
+      "dev": true
     },
     "lodash.memoize": {
       "version": "3.0.4",
@@ -49253,16 +49278,6 @@
       "integrity": "sha512-hdN1wVrZbb29eBGiGjJbeP8JbKjq1urkHJ/LIP/NY48MZ1QVXUsQBV1G1zvYFHn1XE06cwjBsOI2K3Ulnj1YXQ==",
       "optional": true
     },
-    "md5": {
-      "version": "2.3.0",
-      "resolved": "https://registry.npmjs.org/md5/-/md5-2.3.0.tgz",
-      "integrity": "sha512-T1GITYmFaKuO91vxyoQMFETst+O71VUPEU3ze5GNzDm0OWdP8v1ziTaAEPUr/3kLsY3Sftgz242A1SetQiDL7g==",
-      "requires": {
-        "charenc": "0.0.2",
-        "crypt": "0.0.2",
-        "is-buffer": "~1.1.6"
-      }
-    },
     "md5.js": {
       "version": "1.3.5",
       "resolved": "https://registry.npmjs.org/md5.js/-/md5.js-1.3.5.tgz",
@@ -52776,11 +52791,6 @@
       "integrity": "sha512-MXW/jtHyl5F1PZI7NbpS8SOtympdLuF20aoWJT5lELR1p/HJDd5nqW8Eu9uLh/hCRY3FgvrIT5AwDCgBODklcA==",
       "dev": true
     },
-    "remove-trailing-slash": {
-      "version": "0.1.1",
-      "resolved": "https://registry.npmjs.org/remove-trailing-slash/-/remove-trailing-slash-0.1.1.tgz",
-      "integrity": "sha512-o4S4Qh6L2jpnCy83ysZDau+VORNvnFw07CKSAymkd6ICNVEPisMyzlc00KlvvicsxKck94SEwhDnMNdICzO+tA=="
-    },
     "renderkid": {
       "version": "3.0.0",
       "resolved": "https://registry.npmjs.org/renderkid/-/renderkid-3.0.0.tgz",
diff --git a/packages/cli-repl/package.json b/packages/cli-repl/package.json
index 9c090c9eb..5ca8ae5de 100644
--- a/packages/cli-repl/package.json
+++ b/packages/cli-repl/package.json
@@ -72,7 +72,7 @@
     "@mongosh/shell-evaluator": "0.0.0-dev.0",
     "@mongosh/snippet-manager": "0.0.0-dev.0",
     "@mongosh/types": "0.0.0-dev.0",
-    "analytics-node": "^5.1.2",
+    "@segment/analytics-node": "^1.3.0",
     "ansi-escape-sequences": "^5.1.2",
     "askcharacter": "^1.0.0",
     "askpassword": "^1.2.4",
@@ -93,7 +93,6 @@
     "@mongodb-js/prettier-config-devtools": "^1.0.1",
     "@mongodb-js/sbom-tools": "^0.5.2",
     "@mongodb-js/tsconfig-mongosh": "^1.0.0",
-    "@types/analytics-node": "^3.1.3",
     "@types/ansi-escape-sequences": "^4.0.0",
     "@types/js-yaml": "^4.0.5",
     "@types/node": "^14.14.6",
diff --git a/packages/cli-repl/src/cli-repl.spec.ts b/packages/cli-repl/src/cli-repl.spec.ts
index f8eb21669..f007d5215 100644
--- a/packages/cli-repl/src/cli-repl.spec.ts
+++ b/packages/cli-repl/src/cli-repl.spec.ts
@@ -1202,6 +1202,7 @@ describe('CliRepl', function () {
         let srv: http.Server;
         let host: string;
         let requests: any[];
+        let totalEventsTracked = 0;
         let telemetryDelay = 0;
         const setTelemetryDelay = (val: number) => {
           telemetryDelay = val;
@@ -1210,6 +1211,7 @@ describe('CliRepl', function () {
         beforeEach(async function () {
           process.env.MONGOSH_ANALYTICS_SAMPLE = 'true';
           requests = [];
+          totalEventsTracked = 0;
           srv = http
             .createServer((req, res) => {
               let body = '';
@@ -1220,8 +1222,9 @@ describe('CliRepl', function () {
                 })
                 .on('end', async () => {
                   requests.push({ req, body });
-                  res.writeHead(200);
+                  totalEventsTracked += JSON.parse(body).batch.length;
                   await delay(telemetryDelay);
+                  res.writeHead(200);
                   res.end('Ok\n');
                 });
             })
@@ -1244,19 +1247,26 @@ describe('CliRepl', function () {
         });
 
         it('timeouts fast', async function () {
-          setTelemetryDelay(10000);
+          // The `httpRequestTimeout` of our Segment Analytics is set to
+          // 1000ms which makes these requests fail as they exceed the timeout.
+          // Segment will silently fail http request errors when tracking and flushing.
+          // This will cause the test to fail if the system running the tests is
+          //  unable to flush telemetry in 1500ms.
+          this.timeout(2500);
+          setTelemetryDelay(5000);
           await cliRepl.start(await testServer.connectionString(), {});
           input.write('use somedb;\n');
           input.write('exit\n');
           await waitBus(cliRepl.bus, 'mongosh:closed');
-          const analyticsLog = (await log()).find(
+          const analyticsLog = (await log()).filter(
             (entry) =>
               entry.ctx === 'analytics' &&
               entry.msg === 'Flushed outstanding data'
           );
-          expect(analyticsLog).to.have.nested.property(
+          expect(analyticsLog).to.have.lengthOf(1);
+          expect(analyticsLog[0]).to.have.nested.property(
             'attr.flushError',
-            'timeout of 1000ms exceeded'
+            null // Although the flush request will time out, it does not error.
           );
         });
 
@@ -1386,7 +1396,7 @@ describe('CliRepl', function () {
           );
           expect(flushEntry.attr.flushError).to.equal(null);
           expect(flushEntry.attr.flushDuration).to.be.a('number');
-          expect(requests).to.have.lengthOf(2);
+          expect(totalEventsTracked).to.equal(4);
         });
 
         it('sends out telemetry data for command line scripts', async function () {
@@ -1396,7 +1406,7 @@ describe('CliRepl', function () {
             cliRepl,
             await testServer.connectionString()
           );
-          expect(requests).to.have.lengthOf(2);
+          expect(totalEventsTracked).to.equal(5);
         });
 
         it('sends out telemetry if the repl is running in an interactive mode in a containerized environment', async function () {
@@ -1408,7 +1418,7 @@ describe('CliRepl', function () {
           input.write('db.hello()\n');
           input.write('exit\n');
           await waitBus(cliRepl.bus, 'mongosh:closed');
-          expect(requests).to.have.lengthOf(2);
+          expect(totalEventsTracked).to.equal(4);
         });
 
         it('does not send out telemetry if the user starts with a no-telemetry config', async function () {
diff --git a/packages/cli-repl/src/cli-repl.ts b/packages/cli-repl/src/cli-repl.ts
index 8bc119455..aaddd7812 100644
--- a/packages/cli-repl/src/cli-repl.ts
+++ b/packages/cli-repl/src/cli-repl.ts
@@ -12,7 +12,7 @@ import type { CliOptions, DevtoolsConnectOptions } from '@mongosh/arg-parser';
 import { SnippetManager } from '@mongosh/snippet-manager';
 import { Editor } from '@mongosh/editor';
 import { redactSensitiveData } from '@mongosh/history';
-import type Analytics from 'analytics-node';
+import type { Analytics as SegmentAnalytics } from '@segment/analytics-node';
 import askpassword from 'askpassword';
 import { EventEmitter, once } from 'events';
 import yaml from 'js-yaml';
@@ -44,7 +44,6 @@ import {
 } from '@mongosh/types';
 import { promises as fs } from 'fs';
 import path from 'path';
-import { promisify } from 'util';
 import { getOsInfo } from './get-os-info';
 import { UpdateNotificationManager } from './update-notification-manager';
 import { getTimingData, markTime, summariseTimingData } from './startup-timing';
@@ -113,7 +112,7 @@ export class CliRepl implements MongoshIOProvider {
   input: Readable;
   output: Writable;
   analyticsOptions?: AnalyticsOptions;
-  segmentAnalytics?: Analytics;
+  segmentAnalytics?: SegmentAnalytics;
   toggleableAnalytics: ToggleableAnalytics = new ToggleableAnalytics();
   warnedAboutInaccessibleFiles = false;
   onExit: (code?: number) => Promise<never>;
@@ -510,17 +509,13 @@ export class CliRepl implements MongoshIOProvider {
     }
     // 'http' is not supported in startup snapshots yet.
     // eslint-disable-next-line @typescript-eslint/no-var-requires
-    const Analytics = require('analytics-node');
-    this.segmentAnalytics = new Analytics(
-      apiKey,
-      {
-        ...this.analyticsOptions,
-        axiosConfig: {
-          timeout: 1000,
-        },
-        axiosRetryConfig: { retries: 0 },
-      } as any /* axiosConfig and axiosRetryConfig are existing options, but don't have type definitions */
-    );
+    const { Analytics } = require('@segment/analytics-node');
+    this.segmentAnalytics = new Analytics({
+      writeKey: apiKey,
+      maxRetries: 0,
+      httpRequestTimeout: 1000,
+      ...this.analyticsOptions,
+    });
     this.toggleableAnalytics = new ToggleableAnalytics(
       new SampledAnalytics({
         target: new ThrottledAnalytics({
@@ -1028,7 +1023,7 @@ export class CliRepl implements MongoshIOProvider {
     if (analytics) {
       const flushStart = Date.now();
       try {
-        await promisify(analytics.flush.bind(analytics))();
+        await analytics.flush();
         markTime(TimingCategories.Telemetry, 'flushed analytics');
       } catch (err: any) {
         flushError = err.message;
diff --git a/packages/logging/src/analytics-helpers.spec.ts b/packages/logging/src/analytics-helpers.spec.ts
index 9efda4e1e..5030e46f0 100644
--- a/packages/logging/src/analytics-helpers.spec.ts
+++ b/packages/logging/src/analytics-helpers.spec.ts
@@ -27,8 +27,8 @@ describe('analytics helpers', function () {
       track(info: any) {
         events.push(['track', info]);
       },
-      flush(cb) {
-        cb();
+      async flush() {
+        return Promise.resolve();
       },
     };
   });
@@ -153,7 +153,7 @@ describe('analytics helpers', function () {
       analytics.track(tEvt);
       analytics.track(tEvt);
       analytics.track(tEvt);
-      await promisify(analytics.flush.bind(analytics))();
+      await analytics.flush();
       expect(events).to.have.lengthOf(5);
     });
 
@@ -166,7 +166,7 @@ describe('analytics helpers', function () {
       for (let i = 0; i < 100; i++) {
         analytics.track(tEvt);
       }
-      await promisify(analytics.flush.bind(analytics))();
+      await analytics.flush();
       expect(events).to.have.lengthOf(5);
     });
 
@@ -184,7 +184,7 @@ describe('analytics helpers', function () {
       for (let i = 0; i < 100; i++) {
         analytics.track(tEvt);
       }
-      await promisify(analytics.flush.bind(analytics))();
+      await analytics.flush();
       expect(events).to.have.lengthOf(10);
     });
 
@@ -199,7 +199,7 @@ describe('analytics helpers', function () {
       a1.identify(iEvt);
       a1.track(tEvt);
       a1.track(tEvt);
-      await promisify(a1.flush.bind(a1))();
+      await a1.flush();
       expect(events).to.have.lengthOf(3);
 
       // second "session"
@@ -211,7 +211,7 @@ describe('analytics helpers', function () {
       for (let i = 0; i < 100; i++) {
         a2.track(tEvt);
       }
-      await promisify(a2.flush.bind(a2))();
+      await a2.flush();
       expect(events).to.have.lengthOf(5);
     });
 
@@ -236,8 +236,8 @@ describe('analytics helpers', function () {
       a1.track(tEvt);
       a2.track(t2Evt);
 
-      await promisify(a1.flush.bind(a1))();
-      await promisify(a2.flush.bind(a2))();
+      await a1.flush();
+      await a2.flush();
 
       expect(events).to.have.lengthOf(4);
       expect(
diff --git a/packages/logging/src/analytics-helpers.ts b/packages/logging/src/analytics-helpers.ts
index dc0b162d8..4bdecf5a3 100644
--- a/packages/logging/src/analytics-helpers.ts
+++ b/packages/logging/src/analytics-helpers.ts
@@ -34,9 +34,7 @@ export interface MongoshAnalytics {
 
   track(message: AnalyticsTrackMessage): void;
 
-  // NB: Callback and not a promise to match segment analytics interface so it's
-  // easier to pass it to the helpers constructor
-  flush(callback: (err?: Error) => void): void;
+  flush(): Promise<void>;
 }
 
 class Queue<T> {
@@ -84,8 +82,8 @@ class Queue<T> {
 export class NoopAnalytics implements MongoshAnalytics {
   identify(): void {}
   track(): void {}
-  flush(cb: () => void) {
-    cb();
+  flush() {
+    return Promise.resolve();
   }
 }
 
@@ -170,8 +168,8 @@ export class ToggleableAnalytics implements MongoshAnalytics {
     }
   }
 
-  flush(callback: (err?: Error | undefined) => void): void {
-    return this._target.flush(callback);
+  async flush(): Promise<void> {
+    return await this._target.flush();
   }
 }
 
@@ -351,31 +349,28 @@ export class ThrottledAnalytics implements MongoshAnalytics {
     return this.throttleState.count < this.throttleOptions.rate;
   }
 
-  flush(callback: (err?: Error | undefined) => void): void {
+  async flush(): Promise<void> {
     if (!this.throttleOptions) {
-      this.target.flush(callback);
+      await this.target.flush();
       return;
     }
 
     if (!this.currentUserId) {
-      callback(
-        new Error('Trying to persist throttle state before userId is set')
-      );
-      return;
+      throw new Error('Trying to persist throttle state before userId is set');
     }
 
-    this.restorePromise.finally(async () => {
-      try {
-        await fs.promises.writeFile(
-          this.metadataPath,
-          JSON.stringify(this.throttleState)
-        );
-        await this.unlock();
-        this.target.flush(callback);
-      } catch (e) {
-        callback(e as Error);
-      }
-    });
+    try {
+      await this.restorePromise;
+    } catch {
+      // Ignored.
+    }
+
+    await fs.promises.writeFile(
+      this.metadataPath,
+      JSON.stringify(this.throttleState)
+    );
+    await this.unlock();
+    await this.target.flush();
   }
 }
 
@@ -405,7 +400,7 @@ export class SampledAnalytics implements MongoshAnalytics {
     this.isEnabled && this.target.track(message);
   }
 
-  flush(callback: (err?: Error | undefined) => void): void {
-    this.target.flush(callback);
+  async flush(): Promise<void> {
+    return await this.target.flush();
   }
 }
diff --git a/packages/logging/src/setup-logger-and-telemetry.spec.ts b/packages/logging/src/setup-logger-and-telemetry.spec.ts
index 7d6dac90a..65d677cb8 100644
--- a/packages/logging/src/setup-logger-and-telemetry.spec.ts
+++ b/packages/logging/src/setup-logger-and-telemetry.spec.ts
@@ -52,7 +52,9 @@ describe('setupLoggerAndTelemetry', function () {
     track(info: any) {
       analyticsOutput.push(['track', info]);
     },
-    flush() {},
+    async flush() {
+      return Promise.resolve();
+    },
   };
 
   beforeEach(function () {