diff --git a/Storage/Storage.xcodeproj/project.pbxproj b/Storage/Storage.xcodeproj/project.pbxproj
index 09a5eac84a1..5d398d14f54 100644
--- a/Storage/Storage.xcodeproj/project.pbxproj
+++ b/Storage/Storage.xcodeproj/project.pbxproj
@@ -17,9 +17,11 @@
 		028296F3237D404F00E84012 /* ProductVariation+CoreDataProperties.swift in Sources */ = {isa = PBXBuildFile; fileRef = 028296EF237D404F00E84012 /* ProductVariation+CoreDataProperties.swift */; };
 		028296F4237D404F00E84012 /* Attribute+CoreDataClass.swift in Sources */ = {isa = PBXBuildFile; fileRef = 028296F0237D404F00E84012 /* Attribute+CoreDataClass.swift */; };
 		028296F5237D404F00E84012 /* Attribute+CoreDataProperties.swift in Sources */ = {isa = PBXBuildFile; fileRef = 028296F1237D404F00E84012 /* Attribute+CoreDataProperties.swift */; };
+		02A098272480D160002F8C7A /* MockCrashLogger.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02A098262480D160002F8C7A /* MockCrashLogger.swift */; };
 		02D45649231CFB27008CF0A9 /* StatsVersionBannerVisibility.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02D45648231CFB27008CF0A9 /* StatsVersionBannerVisibility.swift */; };
 		02DA64172313C26400284168 /* StatsVersionBySite.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02DA64162313C26400284168 /* StatsVersionBySite.swift */; };
 		02DA64192313C2AA00284168 /* StatsVersion.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02DA64182313C2AA00284168 /* StatsVersion.swift */; };
+		02EAB6D72480A86D00FD873C /* CrashLogger.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02EAB6D62480A86D00FD873C /* CrashLogger.swift */; };
 		26577519243D808B003168A5 /* WooCommerceModelV26toV27.xcmappingmodel in Sources */ = {isa = PBXBuildFile; fileRef = 26577518243D808B003168A5 /* WooCommerceModelV26toV27.xcmappingmodel */; };
 		450106892399AC7400E24722 /* TaxClass+CoreDataClass.swift in Sources */ = {isa = PBXBuildFile; fileRef = 450106882399AC7400E24722 /* TaxClass+CoreDataClass.swift */; };
 		4501068B2399AC9B00E24722 /* TaxClass+CoreDataProperties.swift in Sources */ = {isa = PBXBuildFile; fileRef = 4501068A2399AC9B00E24722 /* TaxClass+CoreDataProperties.swift */; };
@@ -156,11 +158,13 @@
 		028296F0237D404F00E84012 /* Attribute+CoreDataClass.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "Attribute+CoreDataClass.swift"; sourceTree = "<group>"; };
 		028296F1237D404F00E84012 /* Attribute+CoreDataProperties.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "Attribute+CoreDataProperties.swift"; sourceTree = "<group>"; };
 		028F00652331605000E6C283 /* Model 20.xcdatamodel */ = {isa = PBXFileReference; lastKnownFileType = wrapper.xcdatamodel; path = "Model 20.xcdatamodel"; sourceTree = "<group>"; };
+		02A098262480D160002F8C7A /* MockCrashLogger.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = MockCrashLogger.swift; sourceTree = "<group>"; };
 		02A9F16A22F9873600EE36EA /* Model 19.xcdatamodel */ = {isa = PBXFileReference; lastKnownFileType = wrapper.xcdatamodel; path = "Model 19.xcdatamodel"; sourceTree = "<group>"; };
 		02D45648231CFB27008CF0A9 /* StatsVersionBannerVisibility.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = StatsVersionBannerVisibility.swift; sourceTree = "<group>"; };
 		02DA64162313C26400284168 /* StatsVersionBySite.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = StatsVersionBySite.swift; sourceTree = "<group>"; };
 		02DA64182313C2AA00284168 /* StatsVersion.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = StatsVersion.swift; sourceTree = "<group>"; };
 		02E4F5E223CD552F003B0010 /* Model 26.xcdatamodel */ = {isa = PBXFileReference; lastKnownFileType = wrapper.xcdatamodel; path = "Model 26.xcdatamodel"; sourceTree = "<group>"; };
+		02EAB6D62480A86D00FD873C /* CrashLogger.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = CrashLogger.swift; sourceTree = "<group>"; };
 		262CD20224317C2F00932241 /* Model 27.xcdatamodel */ = {isa = PBXFileReference; lastKnownFileType = wrapper.xcdatamodel; path = "Model 27.xcdatamodel"; sourceTree = "<group>"; };
 		26577518243D808B003168A5 /* WooCommerceModelV26toV27.xcmappingmodel */ = {isa = PBXFileReference; lastKnownFileType = wrapper.xcmappingmodel; path = WooCommerceModelV26toV27.xcmappingmodel; sourceTree = "<group>"; };
 		450106882399AC7400E24722 /* TaxClass+CoreDataClass.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "TaxClass+CoreDataClass.swift"; sourceTree = "<group>"; };
@@ -326,6 +330,14 @@
 /* End PBXFrameworksBuildPhase section */
 
 /* Begin PBXGroup section */
+		02A098252480D155002F8C7A /* Mocks */ = {
+			isa = PBXGroup;
+			children = (
+				02A098262480D160002F8C7A /* MockCrashLogger.swift */,
+			);
+			path = Mocks;
+			sourceTree = "<group>";
+		};
 		4DD3D0BDDE216A90FC1335D7 /* Pods */ = {
 			isa = PBXGroup;
 			children = (
@@ -402,6 +414,7 @@
 				B52B0F7820AA287C00477698 /* StorageManagerType.swift */,
 				B505F6DF20BEEA8100BB1B69 /* StorageType.swift */,
 				D87F61522265AA230031A13B /* FileStorage.swift */,
+				02EAB6D62480A86D00FD873C /* CrashLogger.swift */,
 			);
 			path = Protocols;
 			sourceTree = "<group>";
@@ -454,6 +467,7 @@
 			isa = PBXGroup;
 			children = (
 				D87F61582265AED70031A13B /* Mock data */,
+				02A098252480D155002F8C7A /* Mocks */,
 				B54CA5C520A4BFC800F38CD1 /* Tools */,
 				B52B0F7D20AA2F1200477698 /* Extensions */,
 				B59E11DC20A9F1E6004121A4 /* CoreData */,
@@ -814,6 +828,7 @@
 				B54CA5BD20A4BD3B00F38CD1 /* NSManagedObjectContext+Storage.swift in Sources */,
 				933A27302222344D00C2143A /* Logging.swift in Sources */,
 				747453A52242C85E00E0B5EE /* ProductDefaultAttribute+CoreDataClass.swift in Sources */,
+				02EAB6D72480A86D00FD873C /* CrashLogger.swift in Sources */,
 				746A9D21214078080013F6FF /* TopEarnerStats+CoreDataClass.swift in Sources */,
 				74B7D6AD20F90CBB002667AC /* OrderNote+CoreDataClass.swift in Sources */,
 				B52B0F7920AA287C00477698 /* StorageManagerType.swift in Sources */,
@@ -892,6 +907,7 @@
 				9302E3AC220E1CE900DA5018 /* CoreDataIterativeMigratorTests.swift in Sources */,
 				B59E11E020A9F5E6004121A4 /* Constants.swift in Sources */,
 				B54CA5C320A4BF6900F38CD1 /* NSManagedObjectContextStorageTests.swift in Sources */,
+				02A098272480D160002F8C7A /* MockCrashLogger.swift in Sources */,
 				B54CA5C720A4BFDC00F38CD1 /* DummyStack.swift in Sources */,
 				B54CA5C220A4BF6900F38CD1 /* NSManagedObjectStorageTests.swift in Sources */,
 				D87F61572265AD980031A13B /* FileStorageTests.swift in Sources */,
diff --git a/Storage/Storage/CoreData/CoreDataManager.swift b/Storage/Storage/CoreData/CoreDataManager.swift
index f25281d7e27..a1380cf4e2d 100644
--- a/Storage/Storage/CoreData/CoreDataManager.swift
+++ b/Storage/Storage/CoreData/CoreDataManager.swift
@@ -10,6 +10,7 @@ public class CoreDataManager: StorageManagerType {
     ///
     public let name: String
 
+    private let crashLogger: CrashLogger
 
     /// Designated Initializer.
     ///
@@ -17,8 +18,9 @@ public class CoreDataManager: StorageManagerType {
     ///
     /// - Important: This should *match* with your actual Data Model file!.
     ///
-    public init(name: String) {
+    public init(name: String, crashLogger: CrashLogger) {
         self.name = name
+        self.crashLogger = crashLogger
     }
 
 
@@ -37,11 +39,11 @@ public class CoreDataManager: StorageManagerType {
         container.persistentStoreDescriptions = [storeDescription]
 
         container.loadPersistentStores { [weak self] (storeDescription, error) in
-            guard let `self` = self, let error = error else {
+            guard let `self` = self, let persistentStoreLoadingError = error else {
                 return
             }
 
-            DDLogError("⛔️ [CoreDataManager] loadPersistentStore failed. Attempting to recover... \(error)")
+            DDLogError("⛔️ [CoreDataManager] loadPersistentStore failed. Attempting to recover... \(persistentStoreLoadingError)")
 
             /// Backup the old Store
             ///
@@ -49,9 +51,28 @@ public class CoreDataManager: StorageManagerType {
                 let sourceURL = self.storeURL
                 let backupURL = sourceURL.appendingPathExtension("~")
                 try FileManager.default.copyItem(at: sourceURL, to: backupURL)
-                try FileManager.default.removeItem(at: sourceURL)
             } catch {
-                fatalError("☠️ [CoreDataManager] Cannot backup Store: \(error)")
+                let message = "☠️ [CoreDataManager] Cannot backup Store: \(error)"
+                self.crashLogger.logMessageAndWait(message,
+                                                   properties: ["persistentStoreLoadingError": persistentStoreLoadingError,
+                                                                "backupError": error,
+                                                                "appState": UIApplication.shared.applicationState.rawValue],
+                                                   level: .fatal)
+                fatalError(message)
+            }
+
+            /// Remove the old Store
+            ///
+            do {
+                try FileManager.default.removeItem(at: self.storeURL)
+            } catch {
+                let message = "☠️ [CoreDataManager] Cannot remove Store: \(error)"
+                self.crashLogger.logMessageAndWait(message,
+                                                   properties: ["persistentStoreLoadingError": persistentStoreLoadingError,
+                                                                "removeStoreError": error,
+                                                                "appState": UIApplication.shared.applicationState.rawValue],
+                                                   level: .fatal)
+                fatalError(message)
             }
 
             /// Retry!
@@ -61,8 +82,19 @@ public class CoreDataManager: StorageManagerType {
                     return
                 }
 
-                fatalError("☠️ [CoreDataManager] Recovery Failed! \(error) [\(error.userInfo)]")
+                let message = "☠️ [CoreDataManager] Recovery Failed! \(error) [\(error.userInfo)]"
+                self?.crashLogger.logMessageAndWait(message,
+                                                    properties: ["persistentStoreLoadingError": persistentStoreLoadingError,
+                                                                 "retryError": error,
+                                                                 "appState": UIApplication.shared.applicationState.rawValue],
+                                                    level: .fatal)
+                fatalError(message)
             }
+
+            self.crashLogger.logMessage("[CoreDataManager] Recovered from persistent store loading error",
+                                        properties: ["persistentStoreLoadingError": persistentStoreLoadingError,
+                                                     "appState": UIApplication.shared.applicationState.rawValue],
+                                        level: .info)
         }
 
         return container
diff --git a/Storage/Storage/Protocols/CrashLogger.swift b/Storage/Storage/Protocols/CrashLogger.swift
new file mode 100644
index 00000000000..5339c2389b7
--- /dev/null
+++ b/Storage/Storage/Protocols/CrashLogger.swift
@@ -0,0 +1,29 @@
+/// The level of severity, that is currently based on `SentrySeverity`.
+public enum SeverityLevel {
+    case fatal
+    case error
+    case warning
+    case info
+    case debug
+}
+
+/// Logs crashes or messages at a given severity level.
+public protocol CrashLogger {
+    /**
+     Writes a message to the Crash Logging system.
+     - Parameters:
+     - message: The message
+     - properties: A dictionary containing additional information about this message
+     - level: The level of severity to report
+    */
+    func logMessage(_ message: String, properties: [String: Any]?, level: SeverityLevel)
+
+    /**
+     Writes a message to the Crash Logging system and waits until the message is sent.
+     - Parameters:
+     - message: The message
+     - properties: A dictionary containing additional information about this message
+     - level: The level of severity to report
+    */
+    func logMessageAndWait(_ message: String, properties: [String: Any]?, level: SeverityLevel)
+}
diff --git a/Storage/StorageTests/CoreData/CoreDataManagerTests.swift b/Storage/StorageTests/CoreData/CoreDataManagerTests.swift
index 20c70b4c5b0..9824751d2ed 100644
--- a/Storage/StorageTests/CoreData/CoreDataManagerTests.swift
+++ b/Storage/StorageTests/CoreData/CoreDataManagerTests.swift
@@ -10,7 +10,7 @@ class CoreDataManagerTests: XCTestCase {
     /// Verifies that the Data Model URL contains the ContextIdentifier String.
     ///
     func testModelUrlMapsToDataModelWithContextIdentifier() {
-        let manager = CoreDataManager(name: "WooCommerce")
+        let manager = CoreDataManager(name: "WooCommerce", crashLogger: MockCrashLogger())
         XCTAssertEqual(manager.modelURL.lastPathComponent, "WooCommerce.momd")
         XCTAssertNoThrow(manager.managedModel)
     }
@@ -18,7 +18,7 @@ class CoreDataManagerTests: XCTestCase {
     /// Verifies that the Store URL contains the ContextIdentifier string.
     ///
     func testStorageUrlMapsToSqliteFileWithContextIdentifier() {
-        let manager = CoreDataManager(name: "WooCommerce")
+        let manager = CoreDataManager(name: "WooCommerce", crashLogger: MockCrashLogger())
         XCTAssertEqual(manager.storeURL.lastPathComponent, "WooCommerce.sqlite")
         XCTAssertEqual(manager.storeDescription.url?.lastPathComponent, "WooCommerce.sqlite")
     }
@@ -26,7 +26,7 @@ class CoreDataManagerTests: XCTestCase {
     /// Verifies that the PersistentContainer properly loads the sqlite database.
     ///
     func testPersistentContainerLoadsExpectedDataModelAndSqliteDatabase() {
-        let manager = CoreDataManager(name: "WooCommerce")
+        let manager = CoreDataManager(name: "WooCommerce", crashLogger: MockCrashLogger())
         let container = manager.persistentContainer
 
         XCTAssertEqual(container.managedObjectModel, manager.managedModel)
@@ -36,14 +36,14 @@ class CoreDataManagerTests: XCTestCase {
     /// Verifies that the ContextManager's viewContext matches the PersistenContainer.viewContext
     ///
     func testViewContextPropertyReturnsPersistentContainerMainContext() {
-        let manager = CoreDataManager(name: "WooCommerce")
+        let manager = CoreDataManager(name: "WooCommerce", crashLogger: MockCrashLogger())
         XCTAssertEqual(manager.viewStorage as? NSManagedObjectContext, manager.persistentContainer.viewContext)
     }
 
     /// Verifies that performBackgroundTask effectively runs received closure in BG.
     ///
     func testPerformTaskInBackgroundEffectivelyRunsReceivedClosureInBackgroundThread() {
-        let manager = CoreDataManager(name: "WooCommerce")
+        let manager = CoreDataManager(name: "WooCommerce", crashLogger: MockCrashLogger())
         let expectation = self.expectation(description: "Background")
 
         manager.performBackgroundTask { (_) in
@@ -57,7 +57,7 @@ class CoreDataManagerTests: XCTestCase {
     /// Verifies that derived context is instantiated correctly.
     ///
     func testDerivedStorageIsInstantiatedCorrectly() {
-        let manager = CoreDataManager(name: "WooCommerce")
+        let manager = CoreDataManager(name: "WooCommerce", crashLogger: MockCrashLogger())
         let viewContext = (manager.viewStorage as? NSManagedObjectContext)
         let derivedContext = (manager.newDerivedStorage() as? NSManagedObjectContext)
 
diff --git a/Storage/StorageTests/Mocks/MockCrashLogger.swift b/Storage/StorageTests/Mocks/MockCrashLogger.swift
new file mode 100644
index 00000000000..b93d3f830e8
--- /dev/null
+++ b/Storage/StorageTests/Mocks/MockCrashLogger.swift
@@ -0,0 +1,11 @@
+import Storage
+
+struct MockCrashLogger: CrashLogger {
+    func logMessage(_ message: String, properties: [String: Any]?, level: SeverityLevel) {
+        // no-op
+    }
+
+    func logMessageAndWait(_ message: String, properties: [String: Any]?, level: SeverityLevel) {
+        // no-op
+    }
+}
diff --git a/WooCommerce/Classes/ServiceLocator/ServiceLocator.swift b/WooCommerce/Classes/ServiceLocator/ServiceLocator.swift
index 5465fb21a92..948b107f4fe 100644
--- a/WooCommerce/Classes/ServiceLocator/ServiceLocator.swift
+++ b/WooCommerce/Classes/ServiceLocator/ServiceLocator.swift
@@ -43,7 +43,7 @@ final class ServiceLocator {
 
     /// CoreData Stack
     ///
-    private static var _storageManager = CoreDataManager(name: WooConstants.databaseStackName)
+    private static var _storageManager = CoreDataManager(name: WooConstants.databaseStackName, crashLogger: SentryCrashLogger())
 
     /// Cocoalumberjack DDLog
     ///
diff --git a/WooCommerce/Classes/Tools/Logging/Dictionary+Logging.swift b/WooCommerce/Classes/Tools/Logging/Dictionary+Logging.swift
new file mode 100644
index 00000000000..42583171d44
--- /dev/null
+++ b/WooCommerce/Classes/Tools/Logging/Dictionary+Logging.swift
@@ -0,0 +1,32 @@
+import Foundation
+
+extension Dictionary where Key == String {
+    /// Manually serializes a value in a dictionary if the value is not already serializable.
+    func serializeValuesForLoggingIfNeeded() -> [String: Any] {
+        guard JSONSerialization.isValidJSONObject(self) == false else {
+            return self
+        }
+
+        return reduce([:]) { (properties, entry) -> [String: Any] in
+            let (key, value) = entry
+            var formattedProperties: [String: Any] = properties
+            guard JSONSerialization.isValidJSONObject([key: value]) == false else {
+                formattedProperties[key] = value
+                return formattedProperties
+            }
+
+            if let nsError = value as? NSError {
+                formattedProperties[key] = [
+                    "Domain": nsError.domain,
+                    "Code": nsError.code,
+                    "Description": nsError.localizedDescription,
+                    "User Info": nsError.userInfo.description
+                ]
+                return formattedProperties
+            }
+
+            formattedProperties[key] = "\(value)"
+            return formattedProperties
+        }
+    }
+}
diff --git a/WooCommerce/Classes/Tools/Logging/SentryCrashLogger.swift b/WooCommerce/Classes/Tools/Logging/SentryCrashLogger.swift
new file mode 100644
index 00000000000..2f803847368
--- /dev/null
+++ b/WooCommerce/Classes/Tools/Logging/SentryCrashLogger.swift
@@ -0,0 +1,62 @@
+import AutomatticTracks
+import Sentry
+import Storage
+
+/// Logs crashes/messages to Sentry.
+final class SentryCrashLogger: CrashLogger {
+    func logMessage(_ message: String, properties: [String: Any]?, level: SeverityLevel) {
+        CrashLogging.logMessage(message, properties: properties?.serializeValuesForLoggingIfNeeded(), level: SentrySeverity(level: level))
+    }
+
+    func logMessageAndWait(_ message: String, properties: [String: Any]?, level: SeverityLevel) {
+        CrashLogging.logMessageAndWait(message, properties: properties?.serializeValuesForLoggingIfNeeded(), level: SentrySeverity(level: level))
+    }
+}
+
+private extension CrashLogging {
+    /**
+     Mostly similar to `logMessage(_:properties:level:)`, but this function blocks the thread until the event is fired.
+     - Parameters:
+     - message: The message
+     - properties: A dictionary containing additional information about this error
+     - level: The level of severity to report in Sentry
+    */
+    static func logMessageAndWait(_ message: String, properties: [String: Any]?, level: SentrySeverity) {
+        let event = Event(level: level)
+        event.message = message
+        event.extra = properties
+
+        Client.shared?.snapshotStacktrace {
+            Client.shared?.appendStacktrace(to: event)
+        }
+
+        guard let client = Client.shared else {
+           return
+        }
+
+        let semaphore = DispatchSemaphore(value: 0)
+
+        client.send(event: event) { _ in
+            semaphore.signal()
+        }
+
+        semaphore.wait()
+    }
+}
+
+private extension SentrySeverity {
+    init(level: SeverityLevel) {
+        switch level {
+        case .fatal:
+            self = .fatal
+        case .error:
+            self = .error
+        case .warning:
+            self = .warning
+        case .info:
+            self = .info
+        case .debug:
+            self = .debug
+        }
+    }
+}
diff --git a/WooCommerce/WooCommerce.xcodeproj/project.pbxproj b/WooCommerce/WooCommerce.xcodeproj/project.pbxproj
index 12f62de712c..c250eae34fe 100644
--- a/WooCommerce/WooCommerce.xcodeproj/project.pbxproj
+++ b/WooCommerce/WooCommerce.xcodeproj/project.pbxproj
@@ -172,6 +172,8 @@
 		0286B27C23C7051F003D784B /* ProductImagesViewController.xib in Resources */ = {isa = PBXBuildFile; fileRef = 0286B27823C7051F003D784B /* ProductImagesViewController.xib */; };
 		0286B27D23C7051F003D784B /* ProductImagesViewController.swift in Sources */ = {isa = PBXBuildFile; fileRef = 0286B27923C7051F003D784B /* ProductImagesViewController.swift */; };
 		0286B27F23C70557003D784B /* ColumnFlowLayout.swift in Sources */ = {isa = PBXBuildFile; fileRef = 0286B27E23C70557003D784B /* ColumnFlowLayout.swift */; };
+		028AFFB32484ED2800693C09 /* Dictionary+Logging.swift in Sources */ = {isa = PBXBuildFile; fileRef = 028AFFB22484ED2800693C09 /* Dictionary+Logging.swift */; };
+		028AFFB62484EDA000693C09 /* Dictionary+LoggingTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 028AFFB52484EDA000693C09 /* Dictionary+LoggingTests.swift */; };
 		028BAC3D22F2DECE008BB4AF /* StoreStatsAndTopPerformersViewController.swift in Sources */ = {isa = PBXBuildFile; fileRef = 028BAC3C22F2DECE008BB4AF /* StoreStatsAndTopPerformersViewController.swift */; };
 		028BAC4022F2EFA5008BB4AF /* StoreStatsAndTopPerformersPeriodViewController.swift in Sources */ = {isa = PBXBuildFile; fileRef = 028BAC3F22F2EFA5008BB4AF /* StoreStatsAndTopPerformersPeriodViewController.swift */; };
 		028BAC4222F30B05008BB4AF /* StoreStatsV4PeriodViewController.swift in Sources */ = {isa = PBXBuildFile; fileRef = 028BAC4122F30B05008BB4AF /* StoreStatsV4PeriodViewController.swift */; };
@@ -242,6 +244,7 @@
 		02EA6BF82435E80600FFF90A /* ImageDownloader.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02EA6BF72435E80600FFF90A /* ImageDownloader.swift */; };
 		02EA6BFA2435E92600FFF90A /* KingfisherImageDownloader+ImageDownloadable.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02EA6BF92435E92600FFF90A /* KingfisherImageDownloader+ImageDownloadable.swift */; };
 		02EA6BFC2435EC3500FFF90A /* MockImageDownloader.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02EA6BFB2435EC3500FFF90A /* MockImageDownloader.swift */; };
+		02EAB6D92480AA4900FD873C /* SentryCrashLogger.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02EAB6D82480AA4900FD873C /* SentryCrashLogger.swift */; };
 		02EEB5C42424AFAA00B8A701 /* TextFieldTableViewCell.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02EEB5C22424AFAA00B8A701 /* TextFieldTableViewCell.swift */; };
 		02EEB5C52424AFAA00B8A701 /* TextFieldTableViewCell.xib in Resources */ = {isa = PBXBuildFile; fileRef = 02EEB5C32424AFAA00B8A701 /* TextFieldTableViewCell.xib */; };
 		02F49ADA23BF356E00FA0BFA /* TitleAndTextFieldTableViewCell.ViewModel+State.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02F49AD923BF356E00FA0BFA /* TitleAndTextFieldTableViewCell.ViewModel+State.swift */; };
@@ -1026,6 +1029,8 @@
 		0286B27823C7051F003D784B /* ProductImagesViewController.xib */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = file.xib; path = ProductImagesViewController.xib; sourceTree = "<group>"; };
 		0286B27923C7051F003D784B /* ProductImagesViewController.swift */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.swift; path = ProductImagesViewController.swift; sourceTree = "<group>"; };
 		0286B27E23C70557003D784B /* ColumnFlowLayout.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = ColumnFlowLayout.swift; sourceTree = "<group>"; };
+		028AFFB22484ED2800693C09 /* Dictionary+Logging.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "Dictionary+Logging.swift"; sourceTree = "<group>"; };
+		028AFFB52484EDA000693C09 /* Dictionary+LoggingTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "Dictionary+LoggingTests.swift"; sourceTree = "<group>"; };
 		028BAC3C22F2DECE008BB4AF /* StoreStatsAndTopPerformersViewController.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = StoreStatsAndTopPerformersViewController.swift; sourceTree = "<group>"; };
 		028BAC3F22F2EFA5008BB4AF /* StoreStatsAndTopPerformersPeriodViewController.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = StoreStatsAndTopPerformersPeriodViewController.swift; sourceTree = "<group>"; };
 		028BAC4122F30B05008BB4AF /* StoreStatsV4PeriodViewController.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = StoreStatsV4PeriodViewController.swift; sourceTree = "<group>"; };
@@ -1096,6 +1101,7 @@
 		02EA6BF72435E80600FFF90A /* ImageDownloader.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = ImageDownloader.swift; sourceTree = "<group>"; };
 		02EA6BF92435E92600FFF90A /* KingfisherImageDownloader+ImageDownloadable.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "KingfisherImageDownloader+ImageDownloadable.swift"; sourceTree = "<group>"; };
 		02EA6BFB2435EC3500FFF90A /* MockImageDownloader.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = MockImageDownloader.swift; sourceTree = "<group>"; };
+		02EAB6D82480AA4900FD873C /* SentryCrashLogger.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SentryCrashLogger.swift; sourceTree = "<group>"; };
 		02EEB5C22424AFAA00B8A701 /* TextFieldTableViewCell.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = TextFieldTableViewCell.swift; sourceTree = "<group>"; };
 		02EEB5C32424AFAA00B8A701 /* TextFieldTableViewCell.xib */ = {isa = PBXFileReference; lastKnownFileType = file.xib; path = TextFieldTableViewCell.xib; sourceTree = "<group>"; };
 		02F49AD923BF356E00FA0BFA /* TitleAndTextFieldTableViewCell.ViewModel+State.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "TitleAndTextFieldTableViewCell.ViewModel+State.swift"; sourceTree = "<group>"; };
@@ -2130,6 +2136,14 @@
 			path = Media;
 			sourceTree = "<group>";
 		};
+		028AFFB42484ED7F00693C09 /* Logging */ = {
+			isa = PBXGroup;
+			children = (
+				028AFFB52484EDA000693C09 /* Dictionary+LoggingTests.swift */,
+			);
+			path = Logging;
+			sourceTree = "<group>";
+		};
 		028BAC4322F3AE3B008BB4AF /* Stats v4 */ = {
 			isa = PBXGroup;
 			children = (
@@ -2740,6 +2754,7 @@
 		B53A569521123D27000776C9 /* Tools */ = {
 			isa = PBXGroup;
 			children = (
+				028AFFB42484ED7F00693C09 /* Logging */,
 				5798191124526FC7000817F8 /* Observables */,
 				D8A8C4F22268288F001C72BF /* AddManualCustomTrackingViewModelTests.swift */,
 				D83F5938225B424B00626E75 /* AddManualTrackingViewModelTests.swift */,
@@ -3102,6 +3117,8 @@
 			children = (
 				933A27362222354600C2143A /* Logging.swift */,
 				B5DB01B42114AB2D00A4F797 /* CrashLogging.swift */,
+				02EAB6D82480AA4900FD873C /* SentryCrashLogger.swift */,
+				028AFFB22484ED2800693C09 /* Dictionary+Logging.swift */,
 			);
 			path = Logging;
 			sourceTree = "<group>";
@@ -4683,6 +4700,7 @@
 				02162729237965E8000208D2 /* ProductFormTableViewModel.swift in Sources */,
 				CE2A9FBF23BFB1BE002BEC1C /* LedgerTableViewCell.swift in Sources */,
 				B58B4AC02108FF6100076FDD /* Array+Helpers.swift in Sources */,
+				028AFFB32484ED2800693C09 /* Dictionary+Logging.swift in Sources */,
 				B5A56BF0219F2CE90065A902 /* VerticalButton.swift in Sources */,
 				748C7780211E18A600814F2C /* OrderStats+Woo.swift in Sources */,
 				D831E2DC230E0558000037D0 /* Authentication.swift in Sources */,
@@ -4748,6 +4766,7 @@
 				B517EA1D218B41F200730EC4 /* String+Woo.swift in Sources */,
 				02564A8C246CE38E00D6DB2A /* SwappableSubviewContainerView.swift in Sources */,
 				024DF31223742B18006658FE /* AztecItalicFormatBarCommand.swift in Sources */,
+				02EAB6D92480AA4900FD873C /* SentryCrashLogger.swift in Sources */,
 				D83F5933225B2EB900626E75 /* ManualTrackingViewController.swift in Sources */,
 				B57C744A20F5649300EEFC87 /* EmptyStoresTableViewCell.swift in Sources */,
 				027D67D1245ADDF40036B8DB /* FilterTypeViewModel+Helpers.swift in Sources */,
@@ -5094,6 +5113,7 @@
 				CECC759923D6160000486676 /* AggregateDataHelperTests.swift in Sources */,
 				020BE76F23B4A468007FE54C /* AztecBlockquoteFormatBarCommandTests.swift in Sources */,
 				748C7784211E2D8400814F2C /* DoubleWooTests.swift in Sources */,
+				028AFFB62484EDA000693C09 /* Dictionary+LoggingTests.swift in Sources */,
 				02A275BE23FE57DC005C560F /* ProductUIImageLoaderTests.swift in Sources */,
 				027B8BBF23FE0F850040944E /* MockMediaStoresManager.swift in Sources */,
 				453770D12431FF4700AC718D /* ProductSettingsViewModelTests.swift in Sources */,
diff --git a/WooCommerce/WooCommerceTests/Tools/Logging/Dictionary+LoggingTests.swift b/WooCommerce/WooCommerceTests/Tools/Logging/Dictionary+LoggingTests.swift
new file mode 100644
index 00000000000..f8be1a96e50
--- /dev/null
+++ b/WooCommerce/WooCommerceTests/Tools/Logging/Dictionary+LoggingTests.swift
@@ -0,0 +1,48 @@
+import XCTest
+@testable import WooCommerce
+
+final class Dictionary_LoggingTests: XCTestCase {
+    func testSerializingValuesForAnEmptyDictionary() {
+        // Arrange
+        let dictionary: [String: Any] = [:]
+
+        // Action
+        let serializableDictionary = dictionary.serializeValuesForLoggingIfNeeded()
+
+        // Assert
+        XCTAssertTrue(JSONSerialization.isValidJSONObject(serializableDictionary))
+        XCTAssertEqual(serializableDictionary.count, 0)
+    }
+
+    func testSerializingValuesForADictionaryWithNSErrors() {
+        // Arrange
+        let error = NSError(domain: "Testing crash logging in Sentry on Reviews tab launch",
+                            code: 100,
+                            userInfo: ["reason": "Testing only"])
+        let error1Key = "Error 1"
+        let error2Key = "Error 2"
+        let dictionary: [String: Any] = [error1Key: error, error2Key: error, "message": "hello"]
+
+        // Action
+        let serializableDictionary = dictionary.serializeValuesForLoggingIfNeeded()
+
+        // Assert
+        XCTAssertTrue(JSONSerialization.isValidJSONObject(serializableDictionary))
+        XCTAssertEqual(serializableDictionary.count, 3)
+    }
+
+    func testSerializingValuesForADictionaryWithUnsupportedType() {
+        // Arrange
+        struct Value {
+            let message: String
+        }
+        let dictionary: [String: Any] = ["test": Value(message: "😃")]
+
+        // Action
+        let serializableDictionary = dictionary.serializeValuesForLoggingIfNeeded()
+
+        // Assert
+        XCTAssertTrue(JSONSerialization.isValidJSONObject(serializableDictionary))
+        XCTAssertEqual(serializableDictionary.count, 1)
+    }
+}
diff --git a/Yosemite/Yosemite.xcodeproj/project.pbxproj b/Yosemite/Yosemite.xcodeproj/project.pbxproj
index ddb3af97380..1df6c63975d 100644
--- a/Yosemite/Yosemite.xcodeproj/project.pbxproj
+++ b/Yosemite/Yosemite.xcodeproj/project.pbxproj
@@ -47,6 +47,7 @@
 		026D52C0238235930092AE05 /* ProductVariationStoreTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 026D52BF238235930092AE05 /* ProductVariationStoreTests.swift */; };
 		028BCE2422DE22BB00056966 /* SiteVisitStatsStoreErrorTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 028BCE2322DE22BB00056966 /* SiteVisitStatsStoreErrorTests.swift */; };
 		029B00A7230D64E800B0AE66 /* StatsTimeRangeTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 029B00A6230D64E800B0AE66 /* StatsTimeRangeTests.swift */; };
+		02A098242480D0D8002F8C7A /* MockCrashLogger.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02A098232480D0D8002F8C7A /* MockCrashLogger.swift */; };
 		02BA23C222EEEABC009539E7 /* AvailabilityStore.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02BA23C122EEEABC009539E7 /* AvailabilityStore.swift */; };
 		02BA23C422EEEB3B009539E7 /* AvailabilityAction.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02BA23C322EEEB3B009539E7 /* AvailabilityAction.swift */; };
 		02BA23C622EEF092009539E7 /* StatsV4AvailabilityStoreTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 02BA23C522EEF092009539E7 /* StatsV4AvailabilityStoreTests.swift */; };
@@ -280,6 +281,7 @@
 		026D52BF238235930092AE05 /* ProductVariationStoreTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = ProductVariationStoreTests.swift; sourceTree = "<group>"; };
 		028BCE2322DE22BB00056966 /* SiteVisitStatsStoreErrorTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SiteVisitStatsStoreErrorTests.swift; sourceTree = "<group>"; };
 		029B00A6230D64E800B0AE66 /* StatsTimeRangeTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = StatsTimeRangeTests.swift; sourceTree = "<group>"; };
+		02A098232480D0D8002F8C7A /* MockCrashLogger.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = MockCrashLogger.swift; sourceTree = "<group>"; };
 		02BA23C122EEEABC009539E7 /* AvailabilityStore.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AvailabilityStore.swift; sourceTree = "<group>"; };
 		02BA23C322EEEB3B009539E7 /* AvailabilityAction.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AvailabilityAction.swift; sourceTree = "<group>"; };
 		02BA23C522EEF092009539E7 /* StatsV4AvailabilityStoreTests.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = StatsV4AvailabilityStoreTests.swift; sourceTree = "<group>"; };
@@ -991,6 +993,7 @@
 				0202B6962387AFBF00F3EBE0 /* MockInMemoryStorage.swift */,
 				020220E32396969E00290165 /* MockProduct.swift */,
 				0248B36A2459127200A271A4 /* MockupNetwork+Path.swift */,
+				02A098232480D0D8002F8C7A /* MockCrashLogger.swift */,
 			);
 			path = Mockups;
 			sourceTree = "<group>";
@@ -1382,6 +1385,7 @@
 				029B00A7230D64E800B0AE66 /* StatsTimeRangeTests.swift in Sources */,
 				02E493ED245C0EBC000AEA9E /* Product+SettingsTests.swift in Sources */,
 				0248B36924590FC300A271A4 /* ProductStore+FilterProductsTests.swift in Sources */,
+				02A098242480D0D8002F8C7A /* MockCrashLogger.swift in Sources */,
 				02FF055F23D985710058E6E7 /* URL+MediaTests.swift in Sources */,
 				02124DAC24318D6B00980D74 /* Media+MediaTypeTests.swift in Sources */,
 				025CA2D0238F54E800B05C81 /* ProductShippingClassStoreTests.swift in Sources */,
diff --git a/Yosemite/YosemiteTests/Mockups/MockCrashLogger.swift b/Yosemite/YosemiteTests/Mockups/MockCrashLogger.swift
new file mode 100644
index 00000000000..b93d3f830e8
--- /dev/null
+++ b/Yosemite/YosemiteTests/Mockups/MockCrashLogger.swift
@@ -0,0 +1,11 @@
+import Storage
+
+struct MockCrashLogger: CrashLogger {
+    func logMessage(_ message: String, properties: [String: Any]?, level: SeverityLevel) {
+        // no-op
+    }
+
+    func logMessageAndWait(_ message: String, properties: [String: Any]?, level: SeverityLevel) {
+        // no-op
+    }
+}
diff --git a/Yosemite/YosemiteTests/Tools/ShippingSettings/StorageShippingSettingsServiceTests.swift b/Yosemite/YosemiteTests/Tools/ShippingSettings/StorageShippingSettingsServiceTests.swift
index 40c8f02ab7c..8a5dee023a6 100644
--- a/Yosemite/YosemiteTests/Tools/ShippingSettings/StorageShippingSettingsServiceTests.swift
+++ b/Yosemite/YosemiteTests/Tools/ShippingSettings/StorageShippingSettingsServiceTests.swift
@@ -10,7 +10,12 @@ final class StorageShippingSettingsServiceTests: XCTestCase {
 
     override func setUp() {
         super.setUp()
-        storage = CoreDataManager(name: "WooCommerce")
+        storage = CoreDataManager(name: "WooCommerce", crashLogger: MockCrashLogger())
+    }
+
+    override func tearDown() {
+        storage = nil
+        super.tearDown()
     }
 
     func testInitialShippingSettings() {