diff --git a/src/lib/extract/extract-access.ts b/src/lib/extract/extract-access.ts
index 3bb4c971..5021e409 100644
--- a/src/lib/extract/extract-access.ts
+++ b/src/lib/extract/extract-access.ts
@@ -28,7 +28,10 @@ export default async function extractAccess(dir: string) {
 
     await writeToFile('access', response, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_access'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-assets.ts b/src/lib/extract/extract-assets.ts
index 06897a4e..04d88b62 100644
--- a/src/lib/extract/extract-assets.ts
+++ b/src/lib/extract/extract-assets.ts
@@ -36,10 +36,16 @@ export async function downloadAllFiles(dir: string) {
 
     const fileList = await getAssetList()
     await Promise.all(fileList.map(file => downloadFile(file, dir).catch(error => {
-      catchError(`Error downloading ${file.filename_disk}: ${error.message}`)
+      catchError(`Error downloading ${file.filename_disk}: ${error.message}`, {
+        context: {fileId: file.id, filename: file.filename_disk, operation: 'downloadFile'},
+        fatal: false,
+      })
     })))
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_assets'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-collections.ts b/src/lib/extract/extract-collections.ts
index 54ab6d46..f951536e 100644
--- a/src/lib/extract/extract-collections.ts
+++ b/src/lib/extract/extract-collections.ts
@@ -19,7 +19,10 @@ export default async function extractCollections(dir: string) {
     )
     await writeToFile('collections', collections, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_collections'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-content.ts b/src/lib/extract/extract-content.ts
index b334de37..71e71579 100644
--- a/src/lib/extract/extract-content.ts
+++ b/src/lib/extract/extract-content.ts
@@ -19,7 +19,10 @@ async function getDataFromCollection(collection: string, dir: string) {
     const response = await api.client.request(readItems(collection as never, {limit: -1}))
     await writeToFile(`${collection}`, response, `${dir}/content/`)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_content'},
+      fatal: true,
+    })
   }
 }
 
@@ -29,7 +32,10 @@ export async function extractContent(dir: string) {
     const collections = await getCollections()
     await Promise.all(collections.map(collection => getDataFromCollection(collection, dir)))
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_content'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-dashboards.ts b/src/lib/extract/extract-dashboards.ts
index b1b979bc..73278c2b 100644
--- a/src/lib/extract/extract-dashboards.ts
+++ b/src/lib/extract/extract-dashboards.ts
@@ -19,7 +19,10 @@ export async function extractDashboards(dir: string) {
     const dashboards = filterFields(response, directusDashboardFields)
     await writeToFile('dashboards', dashboards, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_dashboards'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
@@ -36,7 +39,10 @@ export async function extractPanels(dir: string) {
     const panels = filterFields(response, directusPanelFields)
     await writeToFile('panels', panels, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_dashboards'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-extensions.ts b/src/lib/extract/extract-extensions.ts
index 1d2965f6..346fe1e2 100644
--- a/src/lib/extract/extract-extensions.ts
+++ b/src/lib/extract/extract-extensions.ts
@@ -16,7 +16,10 @@ export default async function extractExtensions(dir: string) {
     const response = await api.client.request(readExtensions())
     await writeToFile('extensions', response, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_extensions'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-fields.ts b/src/lib/extract/extract-fields.ts
index 53022037..0e6697ef 100644
--- a/src/lib/extract/extract-fields.ts
+++ b/src/lib/extract/extract-fields.ts
@@ -34,7 +34,10 @@ export default async function extractFields(dir: string) {
 
     await writeToFile('fields', fields, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_fields'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-files.ts b/src/lib/extract/extract-files.ts
index 67808a1d..f9de8710 100644
--- a/src/lib/extract/extract-files.ts
+++ b/src/lib/extract/extract-files.ts
@@ -19,7 +19,10 @@ export default async function extractFiles(dir: string) {
     const files = filterFields(response, directusFileFields)
     await writeToFile('files', files, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_files'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-flows.ts b/src/lib/extract/extract-flows.ts
index f46f1243..60d58148 100644
--- a/src/lib/extract/extract-flows.ts
+++ b/src/lib/extract/extract-flows.ts
@@ -19,7 +19,10 @@ export async function extractFlows(dir: string) {
     const flows = filterFields(response, directusFlowFields)
     await writeToFile('flows', flows, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_flows'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
@@ -36,7 +39,10 @@ export async function extractOperations(dir: string) {
     const operations = filterFields(response, directusOperationFields)
     await writeToFile('operations', operations, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_flows'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-folders.ts b/src/lib/extract/extract-folders.ts
index 2bd3d68c..d1118e9b 100644
--- a/src/lib/extract/extract-folders.ts
+++ b/src/lib/extract/extract-folders.ts
@@ -19,7 +19,10 @@ export default async function extractFolders(dir: string) {
     const folders = filterFields(response, directusFolderFields)
     await writeToFile('folders', folders, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_folders'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-permissions.ts b/src/lib/extract/extract-permissions.ts
index 59fbd108..ab4932b7 100644
--- a/src/lib/extract/extract-permissions.ts
+++ b/src/lib/extract/extract-permissions.ts
@@ -27,7 +27,10 @@ export default async function extractPermissions(dir: string) {
     })
     await writeToFile('permissions', response, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_permissions'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-policies.ts b/src/lib/extract/extract-policies.ts
index 1923c922..58ebd55c 100644
--- a/src/lib/extract/extract-policies.ts
+++ b/src/lib/extract/extract-policies.ts
@@ -24,7 +24,10 @@ export default async function extractPolicies(dir: string) {
 
     await writeToFile('policies', response, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_policies'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-presets.ts b/src/lib/extract/extract-presets.ts
index 792e5b02..41ce2cce 100644
--- a/src/lib/extract/extract-presets.ts
+++ b/src/lib/extract/extract-presets.ts
@@ -30,7 +30,10 @@ export default async function extractPresets(dir: string) {
     })
     await writeToFile('presets', presets, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_presets'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-relations.ts b/src/lib/extract/extract-relations.ts
index 52cf51dd..73c8f551 100644
--- a/src/lib/extract/extract-relations.ts
+++ b/src/lib/extract/extract-relations.ts
@@ -40,7 +40,10 @@ export default async function extractRelations(dir: string) {
 
     await writeToFile('relations', relations, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_relations'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-roles.ts b/src/lib/extract/extract-roles.ts
index 41f88e58..f1946368 100644
--- a/src/lib/extract/extract-roles.ts
+++ b/src/lib/extract/extract-roles.ts
@@ -19,7 +19,10 @@ export default async function extractRoles(dir: string) {
     const roles = filterFields(response, directusRoleFields)
     await writeToFile('roles', roles, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_roles'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-schema.ts b/src/lib/extract/extract-schema.ts
index d55dcd4b..206f99e4 100644
--- a/src/lib/extract/extract-schema.ts
+++ b/src/lib/extract/extract-schema.ts
@@ -19,7 +19,10 @@ export default async function extractSchema(dir: string) {
     const schema = await api.client.request(schemaSnapshot())
     await writeToFile('schema/snapshot', schema, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_schema'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-settings.ts b/src/lib/extract/extract-settings.ts
index 9c397cbe..99b745d2 100644
--- a/src/lib/extract/extract-settings.ts
+++ b/src/lib/extract/extract-settings.ts
@@ -16,7 +16,10 @@ export default async function extractSettings(dir: string) {
     const settings = await api.client.request(readSettings({limit: -1}))
     await writeToFile('settings', settings, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_settings'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-translations.ts b/src/lib/extract/extract-translations.ts
index 8ce5d64f..3f41c4c1 100644
--- a/src/lib/extract/extract-translations.ts
+++ b/src/lib/extract/extract-translations.ts
@@ -16,7 +16,10 @@ export default async function extractTranslations(dir: string) {
     const translations = await api.client.request(readTranslations({limit: -1}))
     await writeToFile('translations', translations, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_translations'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/extract/extract-users.ts b/src/lib/extract/extract-users.ts
index f9be1b2c..515dd825 100644
--- a/src/lib/extract/extract-users.ts
+++ b/src/lib/extract/extract-users.ts
@@ -19,7 +19,10 @@ export default async function extractUsers(dir: string) {
     const users = filterFields(response, directusUserFields)
     await writeToFile('users', users, dir)
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'extract_users'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/load/load-collections.ts b/src/lib/load/load-collections.ts
index f5ef0652..62d4fbd9 100644
--- a/src/lib/load/load-collections.ts
+++ b/src/lib/load/load-collections.ts
@@ -38,7 +38,10 @@ async function processCollections(collectionsToAdd: any[], fieldsToAdd: any[]) {
 
       await (existingCollection ? addNewFieldsToExistingCollection(collection.collection, fieldsToAdd, existingFields) : addNewCollectionWithFields(collection, fieldsToAdd))
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_collections'},
+      fatal: true,
+    })
     }
   }
 }
@@ -85,7 +88,10 @@ async function addNewFieldsToExistingCollection(collectionName: string, fieldsTo
         // @ts-ignore - ignore
         await api.client.request(createField(collectionName, field))
       } catch (error) {
-        catchError(error)
+        catchError(error, {
+      context: {operation: 'load_collections'},
+      fatal: true,
+    })
       }
     }
   }
@@ -103,7 +109,10 @@ async function updateCollections(collections: any[]) {
         await api.client.request(updateCollection(collection.collection, pl))
       }
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_collections'},
+      fatal: true,
+    })
     }
   }
 }
@@ -126,7 +135,10 @@ async function addCustomFieldsOnSystemCollections(fields: any[]) {
         await api.client.request(createField(field.collection, field))
       }
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_collections'},
+      fatal: true,
+    })
     }
   }
 }
diff --git a/src/lib/load/load-dashboards.ts b/src/lib/load/load-dashboards.ts
index 6ca623ce..3c49fcbd 100644
--- a/src/lib/load/load-dashboards.ts
+++ b/src/lib/load/load-dashboards.ts
@@ -33,7 +33,10 @@ export default async function loadDashboards(dir: string) {
       try {
         await api.client.request(createDashboard(dashboard))
       } catch (error) {
-        catchError(error)
+        catchError(error, {
+      context: {operation: 'load_dashboards'},
+      fatal: true,
+    })
       }
     }))
 
@@ -64,7 +67,10 @@ export async function loadPanels(dir: string) {
     try {
       await api.client.request(createPanel(panel))
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_dashboards'},
+      fatal: true,
+    })
     }
   }))
 }
diff --git a/src/lib/load/load-data.ts b/src/lib/load/load-data.ts
index 848faf27..d2bc9b48 100644
--- a/src/lib/load/load-data.ts
+++ b/src/lib/load/load-data.ts
@@ -79,7 +79,10 @@ async function getExistingPrimaryKeys(collection: string, primaryKeyField: strin
       if (response.length < limit) break
       page++
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_data'},
+      fatal: true,
+    })
       break
     }
   }
@@ -91,7 +94,10 @@ async function uploadBatch(collection: string, batch: any[], method: Function) {
   try {
     await api.client.request(method(collection, batch))
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'load_data'},
+      fatal: true,
+    })
   }
 }
 
@@ -134,7 +140,10 @@ async function loadSingletons(dir:string) {
 
       await api.client.request(updateSingleton(name, cleanedData))
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_data'},
+      fatal: true,
+    })
     }
   }))
 
diff --git a/src/lib/load/load-extensions.ts b/src/lib/load/load-extensions.ts
index 7c956529..ee9bd871 100644
--- a/src/lib/load/load-extensions.ts
+++ b/src/lib/load/load-extensions.ts
@@ -52,7 +52,10 @@ export default async function loadExtensions(dir: string): Promise<void> {
             })
             return `-- Installed ${ext.schema?.name}`
           } catch (error) {
-            catchError(error)
+            catchError(error, {
+      context: {operation: 'load_extensions'},
+      fatal: true,
+    })
             return `-- Failed to install ${ext.schema?.name}`
           }
         }))
diff --git a/src/lib/load/load-files.ts b/src/lib/load/load-files.ts
index 7d6c4760..eb5c2719 100644
--- a/src/lib/load/load-files.ts
+++ b/src/lib/load/load-files.ts
@@ -54,11 +54,17 @@ export default async function loadFiles(dir: string) {
         try {
           await api.client.request(uploadFiles(form as any))
         } catch (error) {
-          catchError(error)
+          catchError(error, {
+      context: {operation: 'load_files'},
+      fatal: true,
+    })
         }
       }))
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_files'},
+      fatal: true,
+    })
     }
   }
 
diff --git a/src/lib/load/load-flows.ts b/src/lib/load/load-flows.ts
index d4817897..0172e984 100644
--- a/src/lib/load/load-flows.ts
+++ b/src/lib/load/load-flows.ts
@@ -39,7 +39,10 @@ export default async function loadFlows(dir: string) {
 
       await loadOperations(newOperations)
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_flows'},
+      fatal: true,
+    })
     } finally {
       ux.action.stop()
     }
@@ -72,6 +75,9 @@ export async function loadOperations(operations: any[]) {
       }
     }
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'load_flows'},
+      fatal: true,
+    })
   }
 }
diff --git a/src/lib/load/load-folders.ts b/src/lib/load/load-folders.ts
index 87fb2525..9917e503 100644
--- a/src/lib/load/load-folders.ts
+++ b/src/lib/load/load-folders.ts
@@ -38,14 +38,20 @@ export default async function loadFolders(dir: string) {
           try {
             await api.client.request(updateFolder(id, rest))
           } catch (error) {
-            catchError(error)
+            catchError(error, {
+      context: {operation: 'load_folders'},
+      fatal: true,
+    })
           }
         }))
       } else {
         // ux.stdout('-- No new folders to create')
       }
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_folders'},
+      fatal: true,
+    })
     }
   }
 
diff --git a/src/lib/load/load-permissions.ts b/src/lib/load/load-permissions.ts
index 905c0cbc..23c891da 100644
--- a/src/lib/load/load-permissions.ts
+++ b/src/lib/load/load-permissions.ts
@@ -30,7 +30,10 @@ export default async function loadPermissions(
         await api.client.request(createPermissions(newPermissions))
       }
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_permissions'},
+      fatal: true,
+    })
     }
   }
 
diff --git a/src/lib/load/load-policies.ts b/src/lib/load/load-policies.ts
index 52b7883b..72c5e91b 100644
--- a/src/lib/load/load-policies.ts
+++ b/src/lib/load/load-policies.ts
@@ -32,7 +32,10 @@ export default async function loadPolicies(dir: string) {
         // Add the new policy ID to our set of existing policies
         existingPolicyIds.add(policy.id)
       } catch (error) {
-        catchError(error)
+        catchError(error, {
+      context: {operation: 'load_policies'},
+      fatal: true,
+    })
       }
     }
   }
diff --git a/src/lib/load/load-presets.ts b/src/lib/load/load-presets.ts
index 4e0be901..71876166 100644
--- a/src/lib/load/load-presets.ts
+++ b/src/lib/load/load-presets.ts
@@ -33,7 +33,10 @@ export default async function loadPresets(dir: string) {
       try {
         await api.client.request(createPresets(presetsToAdd))
       } catch (error) {
-        catchError(error)
+        catchError(error, {
+      context: {operation: 'load_presets'},
+      fatal: true,
+    })
       }
     } else {
     // ux.stdout('-- No new presets to create')
diff --git a/src/lib/load/load-relations.ts b/src/lib/load/load-relations.ts
index 97fe40e5..dca67182 100644
--- a/src/lib/load/load-relations.ts
+++ b/src/lib/load/load-relations.ts
@@ -46,7 +46,10 @@ async function addRelations(relations: any[]) {
     try {
       await api.client.request(createRelation(relation))
     } catch (error) {
-      catchError(error)
+      catchError(error, {
+      context: {operation: 'load_relations'},
+      fatal: true,
+    })
     }
   }
 }
diff --git a/src/lib/load/load-roles.ts b/src/lib/load/load-roles.ts
index 201b8b90..16bb326e 100644
--- a/src/lib/load/load-roles.ts
+++ b/src/lib/load/load-roles.ts
@@ -43,7 +43,10 @@ export default async function loadRoles(dir: string) {
         existingRoleIds.add(role.id)
         existingRoleNames.add(role.name.toLowerCase())
       } catch (error) {
-        catchError(error)
+        catchError(error, {
+      context: {operation: 'load_roles'},
+      fatal: true,
+    })
       }
     }
 
@@ -59,7 +62,10 @@ export default async function loadRoles(dir: string) {
         const simplifiedRole = {parent: role.parent}
         await api.client.request(updateRole(role.id, simplifiedRole))
       } catch (error) {
-        catchError(error)
+        catchError(error, {
+      context: {operation: 'load_roles'},
+      fatal: true,
+    })
       }
     }
   }
diff --git a/src/lib/load/load-settings.ts b/src/lib/load/load-settings.ts
index 78601de1..bd03ff7b 100644
--- a/src/lib/load/load-settings.ts
+++ b/src/lib/load/load-settings.ts
@@ -61,7 +61,10 @@ export default async function loadSettings(dir: string) {
     const mergedSettings = customDefu(currentSettings as any, settings) as DirectusSettings
     await api.client.request(updateSettings(mergedSettings))
   } catch (error) {
-    catchError(error)
+    catchError(error, {
+      context: {operation: 'load_settings'},
+      fatal: true,
+    })
   }
 
   ux.action.stop()
diff --git a/src/lib/load/load-translations.ts b/src/lib/load/load-translations.ts
index 35ca4a2a..c115aff5 100644
--- a/src/lib/load/load-translations.ts
+++ b/src/lib/load/load-translations.ts
@@ -30,7 +30,10 @@ export default async function loadTranslations(dir: string) {
       try {
         await api.client.request(createTranslations(newTranslations))
       } catch (error) {
-        catchError(error)
+        catchError(error, {
+      context: {operation: 'load_translations'},
+      fatal: true,
+    })
       }
     } else {
     // ux.stdout('-- No new translations to create')
diff --git a/src/lib/load/load-users.ts b/src/lib/load/load-users.ts
index 80032281..54e686a0 100644
--- a/src/lib/load/load-users.ts
+++ b/src/lib/load/load-users.ts
@@ -61,7 +61,10 @@ export default async function loadUsers(
       try {
         await api.client.request(createUser(user))
       } catch (error) {
-        catchError(error)
+        catchError(error, {
+      context: {operation: 'load_users'},
+      fatal: true,
+    })
       }
     }
   }