diff --git a/JobTrackerApi.Tests/ProfileCvControllerTests.cs b/JobTrackerApi.Tests/ProfileCvControllerTests.cs
index 76ba7a6..095d596 100644
--- a/JobTrackerApi.Tests/ProfileCvControllerTests.cs
+++ b/JobTrackerApi.Tests/ProfileCvControllerTests.cs
@@ -128,6 +128,53 @@ public sealed class ProfileCvControllerTests
         Assert.Contains(structured.Sections, section => section.Name == "Education");
     }
 
+    [Fact]
+    public async Task Upload_populates_structured_fields_from_flattened_cv_when_ai_json_is_invalid()
+    {
+        var rawExtraction = "connor.babbington@cesnimda.co.uk cesnimda.co.uk +47 41 33 44 70 E D U C A T I O N E X T E N D E D D I P L O M A N V Q L E V E L 3 I N I C T 2012 - 2015 F O L L O W A B O U T M E Mid-level system developer with eight years of experience in UK local government, with expertise in full-stack development, backend, frontend and server administration. I N T E R E S T S I am interested in PC and board games, as well as cooking and learning new skills. E X P E R I E N C E S Y S T E M D E V E L O P E R 2015 - 2023 Developed and maintained multiple full-stack applications using C#, Python, Ruby on Rails, SQL, and JavaScript. + Warwickshire County Council, UK C O N T A C T Native English speaker, Norwegian level A2/B1.";
+
+        var user = new ApplicationUser();
+        var userManager = CreateUserManager();
+        userManager.Setup(x => x.GetUserAsync(It.IsAny<ClaimsPrincipal>())).ReturnsAsync(user);
+        userManager.Setup(x => x.UpdateAsync(user)).ReturnsAsync(IdentityResult.Success);
+        var aiService = new Mock<ISummarizerService>();
+        aiService
+            .Setup(x => x.ExtractTextAsync(It.IsAny<Stream>(), It.IsAny<string>(), It.IsAny<string?>(), It.IsAny<CancellationToken>()))
+            .ReturnsAsync(new AiTextExtractionResult(rawExtraction, false, "application/pdf", 1, rawExtraction.Length, "Resume.en.pdf"));
+        aiService
+            .Setup(x => x.SummarizeSectionAsync(It.Is<string>(instruction => instruction.Contains("Reconstruct this CV text extracted from a PDF", StringComparison.Ordinal)), rawExtraction, 2800, 900))
+            .ReturnsAsync(string.Empty);
+        aiService
+            .Setup(x => x.SummarizeSectionAsync(It.Is<string>(instruction => instruction.Contains("Extract this CV into structured JSON", StringComparison.Ordinal)), It.IsAny<string>(), 3200, 900))
+            .ReturnsAsync("not-json");
+
+        var controller = new ProfileCvController(userManager.Object, aiService.Object)
+        {
+            ControllerContext = new ControllerContext { HttpContext = new DefaultHttpContext() }
+        };
+
+        var bytes = Encoding.UTF8.GetBytes("fake pdf bytes");
+        var file = new FormFile(new MemoryStream(bytes), 0, bytes.Length, "file", "Resume.en.pdf")
+        {
+            Headers = new HeaderDictionary(),
+            ContentType = "application/pdf"
+        };
+
+        var result = await controller.Upload(file);
+
+        Assert.IsType<OkObjectResult>(result);
+        var structured = StructuredCvProfileJson.Deserialize(user.ProfileCvStructureJson);
+        Assert.Equal("Connor Babbington", structured.Contact.FullName);
+        Assert.Equal("connor.babbington@cesnimda.co.uk", structured.Contact.Email);
+        Assert.Equal("+47 41 33 44 70", structured.Contact.Phone);
+        Assert.Contains(structured.Summary, item => item.Contains("eight years of experience", StringComparison.OrdinalIgnoreCase));
+        Assert.Contains(structured.Skills, item => item.Equals("C#", StringComparison.OrdinalIgnoreCase));
+        Assert.Contains(structured.Interests, item => item.Contains("board games", StringComparison.OrdinalIgnoreCase) || item.Contains("cooking", StringComparison.OrdinalIgnoreCase));
+        Assert.Contains(structured.Languages, item => item.Name != null && item.Name.Equals("English", StringComparison.OrdinalIgnoreCase));
+        Assert.Contains(structured.Languages, item => item.Name != null && item.Name.StartsWith("Norwegian", StringComparison.OrdinalIgnoreCase));
+        Assert.DoesNotContain(structured.Sections, section => section.Name == "General");
+    }
+
     [Fact]
     public async Task Parse_returns_structured_cv_and_persists_it()
     {
diff --git a/JobTrackerApi/Controllers/ProfileCvController.cs b/JobTrackerApi/Controllers/ProfileCvController.cs
index 05335ce..eaba01d 100644
--- a/JobTrackerApi/Controllers/ProfileCvController.cs
+++ b/JobTrackerApi/Controllers/ProfileCvController.cs
@@ -231,7 +231,8 @@ public sealed class ProfileCvController : ControllerBase
 
     private async Task<StructuredCvProfile> BuildStructuredCvAsync(string text, CancellationToken cancellationToken)
     {
-        var fallbackSections = ParseSections(text)
+        var parseSource = NormalizeTextForStructuredParsing(text);
+        var fallbackSections = ParseSections(parseSource)
             .Select(section => new StructuredCvSection
             {
                 Name = section.Name,
@@ -240,11 +241,14 @@ public sealed class ProfileCvController : ControllerBase
             })
             .ToList();
 
-        var fallback = StructuredCvProfileJson.FromSections(fallbackSections);
-        fallback.Contact.FullName ??= GuessFullName(text);
-        var extracted = await TryExtractStructuredCvAsync(text, cancellationToken);
+        var sectionFallback = StructuredCvProfileJson.FromSections(fallbackSections);
+        var heuristicFallback = BuildHeuristicStructuredCv(parseSource, text);
+        heuristicFallback.Sections = new List<StructuredCvSection>();
+        var fallback = StructuredCvProfileJson.Merge(heuristicFallback, sectionFallback);
+        fallback.Contact.FullName ??= GuessFullName(text) ?? GuessFullNameFromEmail(fallback.Contact.Email);
+        var extracted = await TryExtractStructuredCvAsync(parseSource, cancellationToken);
         var merged = StructuredCvProfileJson.Merge(extracted, fallback);
-        merged.Contact.FullName ??= GuessFullName(text);
+        merged.Contact.FullName ??= GuessFullName(text) ?? GuessFullNameFromEmail(merged.Contact.Email);
         return StructuredCvProfileJson.Normalize(merged);
     }
 
@@ -305,12 +309,265 @@ public sealed class ProfileCvController : ControllerBase
         return null;
     }
 
+    private static string? GuessFullNameFromEmail(string? email)
+    {
+        if (string.IsNullOrWhiteSpace(email) || !email.Contains('@')) return null;
+        var localPart = email[..email.IndexOf('@')].Trim();
+        if (string.IsNullOrWhiteSpace(localPart)) return null;
+        var parts = Regex.Split(localPart, @"[._-]+")
+            .Select(part => part.Trim())
+            .Where(part => part.Length > 0)
+            .Select(part => char.ToUpperInvariant(part[0]) + part[1..].ToLowerInvariant())
+            .ToList();
+        return parts.Count >= 2 ? string.Join(" ", parts) : null;
+    }
+
+    private static string NormalizeTextForStructuredParsing(string source)
+    {
+        if (string.IsNullOrWhiteSpace(source)) return string.Empty;
+
+        var text = source.Replace("\r\n", "\n").Trim();
+        if (!LooksLikeFlattenedCvExtraction(text)) return text;
+
+        text = Regex.Replace(text, @"\b([A-Z](?:\s+[A-Z]){2,})\b", match =>
+        {
+            var collapsed = Regex.Replace(match.Value, @"\s+", string.Empty);
+            foreach (var alias in SectionAliases)
+            {
+                var aliasLettersOnly = Regex.Replace(alias.Key, @"[^A-Za-z]", string.Empty);
+                if (collapsed.Equals(aliasLettersOnly, StringComparison.OrdinalIgnoreCase))
+                {
+                    return $"\n\n## {alias.Value}\n";
+                }
+            }
+
+            return match.Value;
+        });
+
+        foreach (var alias in SectionAliases.OrderByDescending(pair => pair.Key.Length))
+        {
+            text = Regex.Replace(
+                text,
+                $@"(?<!#)\b{Regex.Escape(alias.Key)}\b",
+                $"\n\n## {alias.Value}\n",
+                RegexOptions.IgnoreCase);
+        }
+
+        text = Regex.Replace(text, @"\s+\+\s+", "\n+ ");
+        text = Regex.Replace(text, @"\s*([•●▪◦])\s*", "\n- ");
+        text = Regex.Replace(text, @"\s+(\d{4}\s*[-–]\s*(?:\d{4}|Present|Current))\b", "\n$1\n", RegexOptions.IgnoreCase);
+        text = Regex.Replace(text, @"\n{3,}", "\n\n");
+
+        return text.Trim();
+    }
+
+    private static StructuredCvProfile BuildHeuristicStructuredCv(string parseSource, string rawSource)
+    {
+        var profile = new StructuredCvProfile();
+        var normalized = parseSource.Replace("\r\n", "\n").Trim();
+
+        profile.Contact.Email = NullIfWhitespace(Regex.Match(rawSource, @"[A-Z0-9._%+-]+@[A-Z0-9.-]+\.[A-Z]{2,}", RegexOptions.IgnoreCase).Value);
+        profile.Contact.Phone = NullIfWhitespace(Regex.Match(rawSource, @"(?<!\w)(?:\+?\d[\d\s().-]{6,}\d)", RegexOptions.IgnoreCase).Value);
+        profile.Contact.Website = NullIfWhitespace(Regex.Match(rawSource, @"\b(?:https?://)?(?:www\.)?[A-Z0-9.-]+\.[A-Z]{2,}(?:/[A-Z0-9._~:/?#\[\]@!$&'()*+,;=-]*)?", RegexOptions.IgnoreCase).Value);
+        profile.Contact.LinkedIn = NullIfWhitespace(Regex.Match(rawSource, @"(?:linkedin(?:\.com)?/[A-Z0-9._~:/?#\[\]@!$&'()*+,;=-]+)", RegexOptions.IgnoreCase).Value);
+        profile.Contact.FullName = GuessFullName(rawSource) ?? GuessFullNameFromEmail(profile.Contact.Email);
+        profile.Contact.Location = NullIfWhitespace(Regex.Match(rawSource, @"\b[A-Z][a-z]+(?:[\s-][A-Z][a-z]+)*,\s*[A-Z][a-z]+(?:\s+[A-Z][a-z]+)*\b").Value);
+
+        var sections = ParseSections(normalized);
+        var summarySection = sections.FirstOrDefault(section => section.Name == "Professional Summary");
+        var flattenedSummary = Regex.Match(
+            rawSource,
+            @"(?:A\s+B\s+O\s+U\s+T\s+M\s+E|P\s+R\s+O\s+F\s+I\s+L\s+E|S\s+U\s+M\s+M\s+A\s+R\s+Y)\s*(?<body>.*?)(?=(?:I\s+N\s+T\s+E\s+R\s+E\s+S\s+T\s+S|E\s+X\s+P\s+E\s+R\s+I\s+E\s+N\s+C\s+E|E\s+D\s+U\s+C\s+A\s+T\s+I\s+O\s+N|C\s+O\s+N\s+T\s+A\s+C\s+T|$))",
+            RegexOptions.IgnoreCase | RegexOptions.Singleline);
+        if (flattenedSummary.Success)
+        {
+            profile.Summary = SplitSentences(flattenedSummary.Groups["body"].Value, 5);
+        }
+        else if (!string.IsNullOrWhiteSpace(summarySection.Content))
+        {
+            profile.Summary = SplitSentences(summarySection.Content, 5);
+        }
+
+        var interestsSection = sections.FirstOrDefault(section => section.Name == "Interests");
+        if (!string.IsNullOrWhiteSpace(interestsSection.Content))
+        {
+            profile.Interests = SplitListLike(interestsSection.Content);
+        }
+        else
+        {
+            var flattenedInterests = Regex.Match(
+                rawSource,
+                @"I\s+N\s+T\s+E\s+R\s+E\s+S\s+T\s+S\s*(?<body>.*?)(?=(?:E\s+X\s+P\s+E\s+R\s+I\s+E\s+N\s+C\s+E|C\s+O\s+N\s+T\s+A\s+C\s+T|E\s+D\s+U\s+C\s+A\s+T\s+I\s+O\s+N|$))",
+                RegexOptions.IgnoreCase | RegexOptions.Singleline);
+            if (flattenedInterests.Success)
+            {
+                profile.Interests = SplitSentences(flattenedInterests.Groups["body"].Value, 4);
+            }
+        }
+
+        var languagesSection = sections.FirstOrDefault(section => section.Name == "Languages");
+        if (!string.IsNullOrWhiteSpace(languagesSection.Content))
+        {
+            profile.Languages = ParseLanguagesHeuristically(languagesSection.Content);
+        }
+        else
+        {
+            profile.Languages = ParseLanguagesHeuristically(rawSource);
+        }
+
+        var skills = new HashSet<string>(StringComparer.OrdinalIgnoreCase);
+        foreach (Match match in Regex.Matches(rawSource, @"(?<![A-Za-z0-9])(?:C#|\.NET|ASP\.NET|SQL|JavaScript|TypeScript|Python|Ruby on Rails|Ruby|React|Azure DevOps|GitHub|CI/CD)(?![A-Za-z0-9])", RegexOptions.IgnoreCase))
+        {
+            skills.Add(match.Value.Trim());
+        }
+        profile.Skills = skills.ToList();
+
+        var educationSection = sections.FirstOrDefault(section => section.Name == "Education");
+        if (!string.IsNullOrWhiteSpace(educationSection.Content))
+        {
+            profile.Education = ParseEducationHeuristically(educationSection.Content);
+        }
+
+        var experienceSection = sections.FirstOrDefault(section => section.Name == "Work Experience");
+        if (!string.IsNullOrWhiteSpace(experienceSection.Content))
+        {
+            profile.Jobs = ParseJobsHeuristically(experienceSection.Content);
+        }
+
+        if (profile.OtherSections.Count == 0 && sections.Any(section => section.Name == "General"))
+        {
+            var general = sections.First(section => section.Name == "General");
+            if (!string.IsNullOrWhiteSpace(general.Content) && profile.Summary.Count == 0)
+            {
+                profile.Summary = SplitSentences(general.Content, 3);
+            }
+        }
+
+        return StructuredCvProfileJson.Normalize(profile);
+    }
+
+    private static List<string> SplitSentences(string content, int limit)
+    {
+        return Regex.Split(content.Replace("\r\n", " "), @"(?<=[.!?])\s+")
+            .Select(value => value.Trim())
+            .Where(value => value.Length > 20)
+            .Take(limit)
+            .ToList();
+    }
+
+    private static List<string> SplitListLike(string content)
+    {
+        return content
+            .Replace("\r\n", "\n")
+            .Split(new[] { '\n', ',', ';' }, StringSplitOptions.RemoveEmptyEntries | StringSplitOptions.TrimEntries)
+            .Select(item => item.Trim().TrimStart('-', '•', '*', ' '))
+            .Where(item => item.Length > 1)
+            .Distinct(StringComparer.OrdinalIgnoreCase)
+            .ToList();
+    }
+
+    private static List<StructuredCvLanguage> ParseLanguagesHeuristically(string content)
+    {
+        var languages = new List<StructuredCvLanguage>();
+        foreach (Match match in Regex.Matches(content, @"\b(English|Norwegian|Norsk|German|French|Spanish|Swedish|Danish)\b(?:[^\n.,;:]*?\b(Native|Fluent|Advanced|Intermediate|Beginner|A1|A2|B1|B2|C1|C2|Native speaker)\b)?", RegexOptions.IgnoreCase))
+        {
+            var name = NullIfWhitespace(match.Groups[1].Value);
+            var level = NullIfWhitespace(match.Groups[2].Value);
+            if (name is null) continue;
+            languages.Add(new StructuredCvLanguage { Name = name, Level = level });
+        }
+
+        return languages
+            .GroupBy(language => language.Name, StringComparer.OrdinalIgnoreCase)
+            .Select(group => group.First())
+            .ToList();
+    }
+
+    private static List<StructuredCvEducation> ParseEducationHeuristically(string content)
+    {
+        var blocks = Regex.Split(content, @"\n\s*\n")
+            .Select(block => block.Trim())
+            .Where(block => block.Length > 0)
+            .ToList();
+
+        var items = new List<StructuredCvEducation>();
+        foreach (var block in blocks)
+        {
+            var lines = block.Split('\n', StringSplitOptions.RemoveEmptyEntries | StringSplitOptions.TrimEntries).ToList();
+            if (lines.Count == 0) continue;
+
+            var dateMatch = Regex.Match(block, @"\b(\d{4})\s*[-–]\s*(\d{4}|Present|Current)\b", RegexOptions.IgnoreCase);
+            var institutionLine = lines.FirstOrDefault(line => line.StartsWith("+ ", StringComparison.Ordinal))?.TrimStart('+', ' ');
+            var qualificationLine = lines.FirstOrDefault(line => !line.StartsWith("+ ", StringComparison.Ordinal) && !Regex.IsMatch(line, @"^\d{4}\s*[-–]"));
+            if (qualificationLine is null && lines.Count > 0) qualificationLine = lines[0];
+
+            if (qualificationLine is null && institutionLine is null) continue;
+            items.Add(new StructuredCvEducation
+            {
+                Qualification = TitleCasePreservingAcronyms(qualificationLine),
+                Institution = TitleCasePreservingAcronyms(institutionLine),
+                Start = dateMatch.Success ? dateMatch.Groups[1].Value : null,
+                End = dateMatch.Success ? dateMatch.Groups[2].Value : null,
+                Details = lines.Where(line => line.StartsWith("- ", StringComparison.Ordinal)).Select(line => line[2..].Trim()).ToList(),
+            });
+        }
+
+        return items;
+    }
+
+    private static List<StructuredCvJob> ParseJobsHeuristically(string content)
+    {
+        var normalized = content.Replace("\r\n", "\n");
+        var pattern = new Regex(@"(?<title>[A-Z][A-Z\s/&-]{3,})\s*\n(?<dates>\d{4}\s*[-–]\s*(?:\d{4}|Present|Current))(?<body>.*?)(?=(?:\n[A-Z][A-Z\s/&-]{3,}\s*\n\d{4}\s*[-–]\s*(?:\d{4}|Present|Current))|\z)", RegexOptions.Singleline);
+        var jobs = new List<StructuredCvJob>();
+
+        foreach (Match match in pattern.Matches(normalized))
+        {
+            var body = match.Groups["body"].Value.Trim();
+            var employer = NullIfWhitespace(Regex.Match(body, @"\+\s*([^\n]+)").Groups[1].Value);
+            var dates = Regex.Split(match.Groups["dates"].Value, @"\s*[-–]\s*");
+            var bullets = SplitSentences(Regex.Replace(body, @"\+\s*[^\n]+", string.Empty), 6);
+
+            jobs.Add(new StructuredCvJob
+            {
+                Title = TitleCasePreservingAcronyms(match.Groups["title"].Value),
+                Company = employer,
+                Start = NullIfWhitespace(dates.FirstOrDefault()),
+                End = NullIfWhitespace(dates.Skip(1).FirstOrDefault()),
+                IsCurrent = string.Equals(dates.Skip(1).FirstOrDefault(), "present", StringComparison.OrdinalIgnoreCase) || string.Equals(dates.Skip(1).FirstOrDefault(), "current", StringComparison.OrdinalIgnoreCase),
+                Bullets = bullets,
+                Skills = bullets.SelectMany(SplitListLike).Where(item => Regex.IsMatch(item, @"^(?:C#|\.NET|ASP\.NET|SQL|JavaScript|TypeScript|Python|Ruby on Rails|Ruby|React|Azure DevOps|GitHub|CI/CD)$", RegexOptions.IgnoreCase)).Distinct(StringComparer.OrdinalIgnoreCase).ToList(),
+            });
+        }
+
+        return jobs;
+    }
+
+    private static string? TitleCasePreservingAcronyms(string? value)
+    {
+        if (string.IsNullOrWhiteSpace(value)) return null;
+
+        var words = value.Trim()
+            .Split(' ', StringSplitOptions.RemoveEmptyEntries)
+            .Select(word => word.Length <= 3 && word.All(char.IsUpper)
+                ? word
+                : char.ToUpperInvariant(word[0]) + word[1..].ToLowerInvariant())
+            .ToArray();
+
+        return string.Join(" ", words);
+    }
+
     private static int CountWords(string? text)
     {
         if (string.IsNullOrWhiteSpace(text)) return 0;
         return text.Trim().Split((char[]?)null, StringSplitOptions.RemoveEmptyEntries).Length;
     }
 
+    private static string? NullIfWhitespace(string? value)
+    {
+        return string.IsNullOrWhiteSpace(value) ? null : value.Trim();
+    }
+
     private static List<(string Name, string Content)> ParseSections(string source)
     {
         var lines = source.Replace("\r\n", "\n").Split('\n');
diff --git a/Models/StructuredCvProfileJson.cs b/Models/StructuredCvProfileJson.cs
index 3d8fcee..d5536f5 100644
--- a/Models/StructuredCvProfileJson.cs
+++ b/Models/StructuredCvProfileJson.cs
@@ -55,12 +55,24 @@ public static class StructuredCvProfileJson
         primary.Contact.Website ??= secondary.Contact.Website;
         primary.Contact.LinkedIn ??= secondary.Contact.LinkedIn;
 
-        if (primary.Summary.Count == 0) primary.Summary = secondary.Summary;
+        primary.Summary = primary.Summary.Count == 0
+            ? secondary.Summary
+            : primary.Summary.Concat(secondary.Summary).Distinct(StringComparer.OrdinalIgnoreCase).ToList();
         if (primary.Jobs.Count == 0) primary.Jobs = secondary.Jobs;
         if (primary.Education.Count == 0) primary.Education = secondary.Education;
-        if (primary.Skills.Count == 0) primary.Skills = secondary.Skills;
-        if (primary.Languages.Count == 0) primary.Languages = secondary.Languages;
-        if (primary.Interests.Count == 0) primary.Interests = secondary.Interests;
+        primary.Skills = primary.Skills.Count == 0
+            ? secondary.Skills
+            : primary.Skills.Concat(secondary.Skills).Distinct(StringComparer.OrdinalIgnoreCase).ToList();
+        primary.Languages = primary.Languages.Count == 0
+            ? secondary.Languages
+            : primary.Languages
+                .Concat(secondary.Languages)
+                .GroupBy(language => language.Name ?? string.Empty, StringComparer.OrdinalIgnoreCase)
+                .Select(group => group.First())
+                .ToList();
+        primary.Interests = primary.Interests.Count == 0
+            ? secondary.Interests
+            : primary.Interests.Concat(secondary.Interests).Distinct(StringComparer.OrdinalIgnoreCase).ToList();
         if (primary.OtherSections.Count == 0) primary.OtherSections = secondary.OtherSections;
         if (primary.Sections.Count == 0) primary.Sections = secondary.Sections;